涉及人名反应的羰基化反应研究进展

doi:10.6023/cjoc202406043

摘要/Abstract

过渡金属催化一氧化碳(CO)或二氧化碳(CO₂)的羰基化过程是构建醛、酯、酰胺、羧酸及醇等高附加值化学品的有效策略之一, 该反应将C1化学化工与石油化工紧密结合, 具有“原子经济性”和对环境友好的优势. 有机人名反应是构建复杂有机分子的重要工具. 基于有机人名反应的重要性, 且羰基化转化过程在该反应中具有十分重要和广泛的应用, 综述了近几年通过发展新型催化剂体系催化羰基化过程在有机人名反应中的研究进展, 包括Reppe反应、羰化偶联反应、Alper羰基化反应、Pauson-Khand反应、Gattermann-Koch甲酰化反应、Koch-Haaf羰基化反应、Semmelhack反应以及Wakamatsu反应. 最后, 对羰基化过程在有机合成中的发展前景以及存在的难点进行了展望, 以期为推动产生新型羰基化过程且实现工业化转化提供借鉴.

关键词: 羰基化反应, 一氧化碳, 有机人名反应, Reppe反应, 羰化偶联反应, Pauson-Khand反应

The carbonylation of carbon monoxide (CO) or carbon dioxide (CO₂) catalyzed by transition metals is one of the effective strategies to construct high-value added chemicals, such as aldehydes, esters, amides, carboxylic acids, alcohols, etc. This reaction combines C1 chemical and petrochemical industries closely with the advantages of “atomic economy” and environmental friendliness. The organic name reaction is an important tool for constructing complex organic molecules. Based on the importance of organic name reactions and the significant application of carbonylation in these reactions, the research progress in recent years through the development of new catalytic systems for carbonylation is reviewed, including Reppe reaction, carbonylation coupling reaction, Alper carbonylation reaction, Pauson-Khand reaction, Gattermann-Koch formylation reaction, Koch-Haaf carbonylation reaction, Semmelhack reaction, and Wakamatsu reaction. Finally, the development and difficulties of carbonylation in organic synthesis are discussed in order to provide reference for promoting the generation of new carbonylation processes and achieving industrial transformation.

Key words: carbonylation, carbon monoxide, organic name reaction, Reppe reaction, carbonylation coupling reaction, Pauson-Khand reaction

引用此文

王耀伟, 王鹏, 史会兵, 张成富, 赵德明, 杨桂爱, 晏耀宗, 冯保林. 涉及人名反应的羰基化反应研究进展[J]. 有机化学, 2025, 45(1): 104-135.

Yaowei Wang, Peng Wang, Huibing Shi, Chengfu Zhang, Deming Zhao, Guiai Yang, Yaozong Yan, Baolin Feng. Research Progress on Carbonylation Involving Name Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 104-135.

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图/表 58

图式1. 羰基化过程在有机人名反应中的应用

Scheme 1. Application of carbonylation in organic name reactions

图式2. Reppe反应

Scheme 2. Reppe reaction

图1. 氢酯化反应中的膦配体

Figure 1. Phosphine ligands in hydroesterification reactions

图式3. 钯催化1,3-二烯烃双氢酯化合成己二酸酯

Scheme 3. Synthesis of adipic acid esters via palladium-catalyzed bi-alkoxycarbonylation of 1,3-dienes

图式4. 氢酯化反应合成α,β-不饱和酯类化合物

Scheme 4. Synthesis of α,β-unsaturated esters by alkoxycarbonylation

图式5. 烯烃高选择性氢酯化反应

Scheme 5. Highly selective alkoxycarbonylation of alkenes

图式6. “钯-芳基双齿膦配体”体系催化烯烃高性能羰基化反应

Scheme 6. High-performance carbonylation of alkenes catalyzed by palladium-aryldiphosphine catalytic system

图式7. 二芳基甲基甲醇或环丙烯的不对称氢酯化反应

Scheme 7. Asymmetric hydroesterification of diarylmethyl carbinols or cyclopropenes

图式8. 酯类化合物的合成

Scheme 8. Synthesis of esters

图式9. 廉价金属催化烷基氯的烷氧羰基化反应

Scheme 9. Low-cost metal catalyzed alkoxycarbonylation of alkyl halides

图式10. 钯催化烯烃与胺的羰化胺化反应

Scheme 10. Pd-catalyzed hydroaminocarbonylation of alkenes with amines

图式11. 铁催化炔烃与碳酸氢铵的氢酰胺化反应

Scheme 11. Iron-catalyzed hydroaminocarbonylation of alkynes with NH4HCO3

图式12. 铜催化的氢酰胺化反应

Scheme 12. Copper-catalyzed hydroaminocarbonylation

图式13. 钯催化烯烃内向异构化氢酰胺化反应

Scheme 13. Palladium-catalyzed inward isomerization hydroaminocarbonylation of alkenes

图式14. 钯催化的双羰化反应

Scheme 14. Double carbonylation catalyzed by Pd

图式15. 烯烃氢羧化反应合成羧酸

Scheme 15. Synthesis of carboxylic acids via hydroxycarbonylation of olefins

图式16. 钯接力催化炔烃不对称双羰基化制备手性琥珀酸

Scheme 16. Asymmetric double hydroxycarbonylation of alkynes to chiral succinic acids enabled by palladium relay catalysis

图式17. 室温条件下钯催化炔烃的高支链选择性氢羧化反应

Scheme 17. Room-temperature palladium-catalyzed hydrocarboxylation of alkynes with high branched selectivity

图式18. 羰化Suzuki偶联反应

Scheme 18. Carbonylative Suzuki cross-coupling reaction

图式19. 膦配体CataCXium A调控的羰化Suzuki偶联反应

Scheme 19. Carbonylative Suzuki cross-coupling reaction regulated by CataCXium A

图式20. Pd-Pincer络合物催化的三组分羰化Suzuki-Miyaura交叉偶联反应

Scheme 20. Pd-Pincer complex catalyzed three-component carbonylative Suzuki-Miyaura cross-coupling reaction

图式21. Pd/NHC配合物催化的羰化Suzuki偶联反应应

Scheme 21. Pd/NHC complexes for carbonylative Suzuki coupling reaction

图式22. Pd-Sn双金属催化的羰化Suzuki、Sonogashira和氨羰基化反应

Scheme 22. Pd-Sn heterobimetallic catalyst for carbonylative Suzuki, Sonogashira and aminocarbonylation reactions

图式23. 羰化Heck偶联反应

Scheme 23. Carbonylative Heck cross-coupling reaction

图式24. 烯烃和邻碘苯胺类化合物的不对称羰化Heck偶联反应

Scheme 24. Enantioselective carbonylative Heck reaction of o-iodoanilines with allenes

图式25. 对映选择性钯催化邻碘烯基苯与芳基硼酸的串联羰化Heck偶联酯化反应

Scheme 25. Enantioselective palladium-catalyzed domino carbonylative Heck esterification of o-iodoalkenylbenzenes with arylboronic acids

图式26. 羰化Stille偶联反应

Scheme 26. Carbonylative Stille cross-coupling reaction

图式27. 无膦配体参与镍催化的羰化Stille偶联反应

Scheme 27. Carbonylative Stille cross-coupling reaction catalyzed by Nickel under phosphine-free condition

图式28. 羰化Negishi偶联反应

Scheme 28. Carbonylative Negishi cross-coupling reaction

图式29. 镍催化烷基锌试剂与异氰酸叔丁酯的烯丙基羰化偶联反应

Scheme 29. Nickel-catalyzed allylic carbonylative coupling of alkyl zinc reagents with tert-butyl isocyanide

图式30. 镍催化非活化烷基亲电试剂的羰化Negishi偶联反应

Scheme 30. Nickel-catalyzed carbonylative Negishi cross-coupling of unactivated secondary alkyl electrophiles

图式31. 羰化Sonogashira偶联反应

Scheme 31. Carbonylative Sonogashira cross-coupling reaction

图式32. 羰化Sonogashira偶联反应合成α,β-不饱和炔酮

Scheme 32. Synthesis of α,β-unsaturated alkyne ketone by carbonylative Sonogashira cross-coupling reaction

图式33. 离子型钯配合物催化的羰化Sonogashira反应

Scheme 33. Carbonylative Sonogashira reaction catalyzed by ionic palladium complex

图式34. 电化学钯催化芳基肼和炔烃的氧化Sonogashira羰化反应

Scheme 34. Electrochemical palladium-catalyzed oxidative Sonogashira carbonylation of arylhydrazines and alkynes

图式35. 三嗪基团加速NHC-Pd催化Sonogashira羰化偶联反应

Scheme 35. Triazine-wingtips accelerated NHC-Pd catalyzed carbonylative Sonogashira cross-coupling reaction

图式36. 钯催化羰化Sonogashira/环化反应合成吲哚并[1,2-b]异喹啉

Scheme 36. Palladium-catalyzed carbonylative Sonogashira/annulation reaction for synthesis of indolo[1,2-b]isoquinolines

图式37. Alper羰基化反应

Scheme 37. Alper carbonylation reaction

图式38. 钯催化2-碘苯胺双羰化反应制备靛红类化合物

Scheme 38. Palladium-catalyzed double carbonylation approach to isatins from 2-iodoanilines

图式39. 芳基碘与酰胺的羰基化: 高效合成环状和无环酰胺

Scheme 39. Carbonylation of aryl iodides with amides: facile synthesis of cyclic and acyclic amides

图式40. 羰基化反应在苯并咪唑[2,1-b]喹唑啉-12-酮合成中的应用

Scheme 40. Carbonylation applied to the synthesis of benzimidazo[2,1-b]quinazolin-12-ones

图式41. Pauson-Khand反应

Scheme 41. Pauson-Khand reaction

图式42. 钌催化的Pauson-Khand反应

Scheme 42. Ruthenium-catalyzed Pauson-Khand reaction

图式43. Rh催化1,6-烯炔和1,7-烯炔的Pauson-Khand反应

Scheme 43. Rhodium-catalyzed Pauson-Khand reaction of 1,6- and 1,7-enynes

图式44. 分子内和分子间的Pauson-Khand反应

Scheme 44. Intra- or intermolecular Pauson-Khand reaction

图2. Pauson-Khand反应合成小分子化合物

Figure 2. Synthesis of small molecules by Pauson-Khand reaction

图式45. 腈类化合物的还原aza-Pauson-Khand反应

Scheme 45. Reductive aza-Pauson-Khand reaction of nitriles

图式46. Gattermann-Koch甲酰化反应

Scheme 46. Gattermann-Koch formylation reaction

图式47. Gattermann-Koch甲酰化反应的应用

Scheme 47. Application of Gattermann-Koch formylation

图式48. 硅离子介导活化CO和芳烃的亲电甲酰化反应

Scheme 48. Electrophilic formylation of arenes by silylium ion mediated activation of CO

图式49. Koch-Haaf反应

Scheme 49. Koch-Haaf reaction

图式50. Koch-Haaf反应的应用

Scheme 50. Application of Koch-Haaf reaction

图式51. Semmelhack反应

Scheme 51. Semmelhack reaction

图式52. Semmelhack反应在白藜芦醇内酯A合成中的应用

Scheme 52. Synthesis of Leucascandrolide A by using Semmelhack reaction

图式53. L利用Semmelhack反应合成Callipeltoside C和4-Dehydroxydiversonol

Scheme 53. Synthesis of callipeltoside C and 4-dehydroxydiversonol by using Semmelhack reaction

图式54. Semmelhack反应在Neopeltolide和Kumausallene合成中的应用

Scheme 54. Synthesis of Neopeltolide and Kumausallene by using Semmelhack reaction

图式55. 利用Semmelhack反应合成白藜芦醇内酯A

Scheme 55. Synthesis of Leucascandrolide A by using Semmel- hack reaction

图式56. 通过Wakamatsu反应合成N-酰基氨基酸

Scheme 56. Synthesis of N-acyl amino-acids by Wakamatsu rea- ction

参考文献 306

[1]	Chen, X. Z.; Chen, G.; Lian, Z. Chin. J. Chem. 2024, 42, 177.
[2]	Peng, J. B.; Liu, X. L.; Li, L.; Wu, X. F. Sci. China: Chem. 2022, 65, 441.
[3]	Zeng, L.; Li, H. R.; Hu, J. C.; Zhang, D. C.; Hu, J. Y.; Peng, P.; Wang, S. C.; Shi, R. Y.; Peng, J. Q.; Pao, C. W.; Chen, J. L.; Lee, J. F.; Zhang, H.; Chen, Y. H.; Lei, A. W. Nat. Catal. 2020, 3, 438.
[4]	Zhao, Z. L.; Gao, G.; Xi, Y. J.; Wang, J.; Sun, P.; Liu, Q.; Yan, W. J.; Cui, Y.; Jiang, Z.; Li, F. W. Chem 2022, 8, 1034.
[5]	Wang, P.; Yang, D.; Liu, H. Chin. J. Org. Chem. 2021, 41, 3448 (in Chinese).
	(王鹏, 杨妲, 刘欢, 有机化学, 2021, 41, 3448.)
[6]	Li, M. B.; Yang, Y.; Rafi, A. A.; Oschmann, M.; Grape, E. S.; Inge, A. K.; Córdova, A.; Bäckvall, J. E. Angew. Chem., Int. Ed. 2020, 59, 10391.
[7]	Weng, Y. Y.; Qu, J. P.; Chen, Y. F. Chin. J. Org. Chem. 2021, 41, 1949 (in Chinese).
	(翁扬扬, 曲景平, 陈宜峰, 有机化学, 2021, 41, 1949.)
[8]	Liu, Y. C.; Chen, Y. H.; Yi, H.; Lei, A. W. ACS Catal. 2022, 12, 7470.
[9]	Peter, G. G.; Thomas, J. C. Organometallics 2015, 34, 5497.
[10]	Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms, Elsevier Academic Press, Burlington, MA, 2005, p. 864.
[11]	Mundy, B. P.; Ellerd, Michael, G.; Favaloro, F. G. Name Reactions and Reagents in Organic Synthesis, 2nd ed., John Wiley & Sons, Hoboken, NJ, 2005, p. 882.
[12]	Laue, T.; Plagens, A. Named Organic Reactions, 2nd ed., John Wiley & Sons, Chichester, England, 2005, p. 320.
[13]	Kiss, G. Chem. Rev. 2001, 101, 3435.
[14]	Sang, R.; Hu, Y. Y.; Razzaq, R.; Jackstell, R.; Franke, R.; Beller, M. Org. Chem. Front. 2021, 8, 799.
[15]	Reppe, W. Liebigs Ann. Chem. 1953, 582, 1.
[16]	Reppe, W.; Kroper, H. Liebigs Ann. Chem. 1953, 582, 38.
[17]	Reppe, W.; Kroper, H.; Kutepow, N.; Pistor, H. Liebigs Ann. Chem. 1953, 582, 72.
[18]	Reppe, W.; Kroper, H.; Pistor, H.; Weissbarth, O. Liebigs Ann. Chem. 1953, 582, 87.
[19]	Reppe, W. Liebigs Ann. Chem. 1953, 582, 116.
[20]	Reppe, W.; Vetter, H. Liebigs Ann. Chem. 1953, 582, 133.
[21]	Bittler, K.; Kutepow, N.; Neubauer, D. V.; Reis, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 329.
[22]	Pugh, R. I.; Drent, E.; Pringle, P. G. Chem. Commun. 2001, 16, 1476.
[23]	Pugh, R. I.; Drent, E. Adv. Synth. Catal. 2002, 344, 837.
[24]	Knight, J. G.; Doherty, S.; Harriman, A.; Robins, E. G.; Betham, M.; Eastham, G. R.; Tooze, R. P.; Elsegood, M. R.; Champkin, P.; Clegg, W. Organometallics 2000, 19, 4957.
[25]	Hou, J.; Yuan, M. L.; Xie, J. H.; Zhou, Q. L. Green Chem. 2016, 18, 2981.
[26]	Fu, M. C.; Shang, R.; Cheng, W. M.; Fu, Y. ACS Catal. 2016, 6, 2501.
[27]	Yang, D.; Liu, L.; Wang, D. L.; Lu, Y.; Zhao, X. L.; Liu, Y. J. Catal. 2019, 371, 236.
[28]	Akao, M.; Sugawara, S.; Amino, K.; Inoue, Y. J. Mol. Catal. A: Chem. 2000, 157, 117.
[29]	Wang, A.; Zhang, L. L.; Yu, Z. N.; Zhang, S. X.; Li, L.; Ren, Y. J.; Yang, J.; Liu, X. Y.; Liu, W.; Yang, X. F.; Zhang, T. Y.; Wang, A. Q. J. Am. Chem. Soc. 2024, 146, 695.
[30]	Imamoto, T.; Yamaguchi, K. Org. Lett. 2006, 8, 6103.
[31]	Drent, E.; Kragtwijk, E. EP 0495548, 1992.
[32]	Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247.
[33]	Clegg, W.; Elsegood, M. R.; Eastham, G. R.; Tooze, R. P.; Wang, X. L.; Whiston, K. Chem. Commun. 1999, 1877.
[34]	Pews-Davtyan, A.; Fang, X.; Jackstell, R.; Spannenberg, A.; Baumann, W.; Franke, R.; Beller, M. Chem.-Asian J. 2014, 9, 1168.
[35]	Li, H.; Dong, K.; Jiao, H.; Neumann, H.; Jackstell, R.; Beller, M. Nat. Chem. 2016, 8, 1159.
[36]	Dong, K.; Fang, X.; Gülak, S.; Franke, R.; Spannenberg, A.; Neumann, H.; Jackstell, R.; Beller, M. Nat. Commun. 2017, 8, 14117.
[37]	Sang, R.; Kucmierczyk, P.; Dong, K.; Franke, R.; Neumann, H.; Jackstell, R.; Beller, M. J. Am. Chem. Soc. 2018, 140, 5217.
[38]	Liu, J.; Dong, K.; Franke, R.; Neumann, H.; Jackstell, R.; Beller, M. Chem. Commun. 2018, 54, 12238.
[39]	Liu, J.; Yang, J.; Baumann, W.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2019, 58, 10683.
[40]	Liu, J.; Yang, J.; Schneider, C.; Franke, R.; Jackstell, R.; Beller, M. Angew. Chem. 2020, 59, 9032.
[41]	Reetz, M. T.; Demuth, R.; Goddard, R. Tetrahedron Lett. 1998, 39, 7089.
[42]	Scrivanti, A.; Beghetto, V.; Campagna, E.; Matteoli, U. J. Mol. Catal. A: Chem. 2001, 168, 75.
[43]	Green, M. J.; Cavell, K. J.; Edwards, P. G.; Tooze, R. P.; Skelton, B. W.; White, A. H. Dalton Trans. 2004, 20, 3251.
[44]	Shuttleworth, T. A.; Miles-Hobbs, A. M.; Pringle, P. G.; Sparkes, H. A. Dalton Trans. 2017, 46, 125.
[45]	Qi, H. M.; Huang, Z. J.; Wang, M. L.; Yang, P. J.; Du, C. X.; Chen, S. W.; Li, Y. H. J. Catal. 2018, 363, 63.
[46]	Yang, J.; Wang, P.; Neumann, H.; Jackstell, R.; Beller, M. Ind. Chem. Mater. 2023, 1, 155.
[47]	Yang, J.; Liu, J. W.; Neumann, H.; Franke, R.; Jackstell, R.; Beller, M. Science 2019, 366, 1514.
[48]	Yang, J.; Liu, J. W.; Ge, Y.; Huang, W. H.; Ferretti, F.; Neumann, H.; Jiao, H. J.; Franke, R.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2021, 60, 9527.
[49]	Yang, D.; Liu, H.; Wang, D. L.; Luo, Z. J.; Lu, Y.; Xia, F.; Liu, Y. Green Chem. 2018, 20, 2588.
[50]	Wang, P.; Shi, H. B.; Feng, B. L.; Zhao, D. M.; Wu, H. G. Monatsh Chem. 2023, 154, 1189.
[51]	Jing, T. H.; Zhao, K. C.; Shi, G. H.; Zhuang, Y. Y.; Chen, X. C.; Zhao, X. L.; Lu, Y.; Liu, Y. J. Catal. 2023, 426, 214.
[52]	Zhao, K.; Wang, H. L.; Li, T.; Liu, S. J.; Benassi, E.; Li, X.; Yao, Y.; Wang, X. J.; Cui, X. J.; Shi, F. Nat. Commun. 2024, 15, 2016.
[53]	Tian, D.; Xu, R.; Zhu, J.; Huang, J.; Dong, W.; Claverie, J.; Tang, W. Angew. Chem., Int. Ed. 2021, 60, 6305.
[54]	Yu, R. R.; Cai, S. Z.; Li, C.; Fang, X. J. Angew. Chem., Int. Ed. 2022, 61, e202200733.
[55]	Yu, W.; Yang, S.; Xiong, F.; Fan, T.; Feng, Y.; Huang, Y.; Fu, J.; Wang, T. Org. Biomol. Chem. 2018, 16, 3099.
[56]	Kim, M.; Yu, S.; Kim, J. G.; Lee, S. Org. Chem. Front. 2018, 5, 2447.
[57]	Tian, Q. Q.; Sun, R. J.; Li, Y. H. Org. Biomol. Chem. 2022, 20, 1186.
[58]	Wang, H.; Li, Y. D.; Sun, Y. J.; Li, Y. H. J. Org. Chem. 2023, 88, 8835.
[59]	Wang, H.; Li, C.; Li, Y. D.; Chen, J. B.; Liu, S. L.; Li, Y. H. Org. Chem. Front. 2024, 11, 1322.
[60]	Ai, H. J.; Leidecker, B. N.; Dam, P.; Kubis, C.; Rabeah, J.; Wu, X. F. Angew. Chem., Int. Ed. 2022, 61, e202211939.
[61]	Ai, H. J.; Geng, H. Q.; Gu, X. W.; Wu, X. F. ACS Catal. 2023, 13, 1310.
[62]	Ai, H. J.; Zhao, F. Q.; Wu, X. F. Chin. J Catal. 2023, 47, 121.
[63]	Ji, X. L.; Gao, B.; Zhou, X. B.; Liu, Z. J.; Huang, H. M. J. Org. Chem. 2018, 83, 10134.
[64]	Sun, Z.; Yan, L.; Ji, G.; Wang, G.; Ma, L.; Jiang, M.; Li, C.; Ding, Y. Appl Catal A: Gen. 2021, 614, 118026.
[65]	Cai, S.; Zhang, H.; Huang, H. Trends Chem. 2021, 3, 218.
[66]	Yao, Y. H.; Yang, H. Y.; Chen, M.; Wu, F.; Xu, X. X.; Guan, Z. H. J. Am. Chem. Soc. 2021, 143, 85.
[67]	Li, J.; Wang, S.; Zou, S.; Huang, H. Commun. Chem. 2019, 2, 14.
[68]	Wei, W. M.; Dong, F. Q.; Zheng, R. H.; Liu, Y. Y.; Zhao, T. T.; Fang, W. J.; Qin, Y. D. Comput. Theor. Chem. 2020, 1191, 113040.
[69]	Liu, Y.; Ding, F.; Chen, Y.; Wu, W.; He, Y. New J. Chem. 2021, 45, 7516.
[70]	Chen, X. C.; Lan, T.; Zhu, J.; Ying, S. B.; Shi, G. H.; Zhao, K. C.; Guo, L.; Lu, Y.; Liu, Y. J. Catal. 2023, 418, 273.
[71]	Bede, F.; Kollár, L.; Lambert, N.; Huszthy, P.; Pongrácz, P. Eur. J. Org. Chem. 2023, 26, e2023005.
[72]	Driller, K. M.; Klein, H.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 6041.
[73]	Liu, H. Z.; Lau, G. P. S.; Dyson, P. J. J. Org. Chem. 2015, 80, 386.
[74]	Yang, J.; Liu, J. W.; Jackstell, R.; Beller, M. Chem. Commun. 2018, 54, 10710.
[75]	Huang, Z.; Tang, C.; Chen, Z.; Pi, S.; Tan, Z.; Deng, J.; Li, Y. J Catal. 2021, 404, 224.
[76]	Huang, Z.; Tang, C.; Chen, Z.; Pi, S.; Tan, Z.; Deng, J.; Li, Y. Chin. Chem. Lett. 2022, 33, 4842.
[77]	Huang, Z. J.; Dong, Y. N.; Jiang, X. L.; Wang, F.; Du, C. X.; Li, Y. H. J. Catal. 2022, 409, 98.
[78]	Geng, H. Q.; Wu, X. F. Chem. Commun. 2022, 58, 6534.
[79]	Yuan, Y.; Zhang, Y.; Li, W.; Zhao, Y.; Wu, X. F. Angew. Chem., Int. Ed. 2023, 62, e2023099.
[80]	Zou, X. J.; Jin, Z. X.; Yang, H. Y.; Wu, F.; Ren, Z. H.; Guan, Z. H. Angew. Chem., Int. Ed. 2024, 63, e202406226.
[81]	Zhang, Y.; Wu, F.; Yang, H. Y.; Wang, G.; Ren, Z. H.; Guan, Z. H. J. Am. Chem. Soc. 2024, 146, 12883.
[82]	Das, D.; Bhanage, B. M. Adv. Synth. Catal. 2020, 362, 3022.
[83]	Ozawa, F.; Soyama, H.; Yamamoto, T.; Yamamoto, A. Tetrahedron Lett. 1982, 23, 3383.
[84]	Kobayashi, T.; Tanaka, M. J. Organomet. Chem. 1982, 233, C64.
[85]	Li, J. H.; Li, G. P.; Jiang, H. F.; Chen, M. C. Tetrahedron Lett. 2001, 42, 6923.
[86]	Sarkar, B. R.; Chaudhari, R. V. Catal. Surv. Asia 2005, 9, 193.
[87]	Tang, C. M.; Zeng, Y.; Yang, X. G.; Lei, Y. C.; Wang, G. Y. J. Mol. Catal. A: Chem. 2009, 314, 15.
[88]	Guo, W. D.; Liu, Y. Prog. Chem. 2021, 33, 512. (in Chinese).
	(郭文迪, 刘晔, 化学进展, 2021, 33, 512.)
[89]	Liu, W.; Huang, W.; Lin, Q.; Tsai, M. H.; Zhang, R.; Fan, L.; Scott, J. D.; Liu, G.; Wan, J. Bioorg. Med. Chem. 2021, 38, 116118.
[90]	Lv, J.; Zong, L.; Zhang, J.; Song, J.; Zhao, J.; Zhang, K.; Zhou, Z.; Gao, M.; Xie, C.; Jia, X.; Ren, X. Catal. Sci. Technol. 2021, 11, 4708.
[91]	Yao, Y. H.; Zou, X. J.; Wang, Y.; Yang, H. Y.; Ren, Z. H.; Guan, Z. H. Angew. Chem., Int. Ed. 2021, 60, 23117.
[92]	Chen, M.; Li, Y.; Guan, Z. H. Org. Lett. 2023, 25, 2571.
[93]	Eliseev, O. L.; Bondarenko, T. N.; Tsapkina, M. V. Mendeleev Commun. 2022, 32, 253.
[94]	Du, M.; Li, Y. Chin. J. Org. Chem. 2022, 42, 3010 (in Chinese).
	(杜民兴, 李跃辉, 有机化学, 2022, 42, 3010.)
[95]	Shao, C.; Lu, A.; Wang, X.; Zhou, B.; Guan, X.; Zhang, Y. Org. Biomol. Chem. 2017, 15, 5033.
[96]	Dühren, R.; Kucmierczyk, P.; Jackstell, R.; Frankebc, R.; Beller, M. Catal. Sci. Technol. 2021, 11, 2026.
[97]	Schneider, C.; Franke, R.; Jackstell, R.; Beller, M. Catal. Sci. Technol. 2021, 11, 2703.
[98]	Ji, X.; Shen, C.; Tian, X.; Dong, K. Org. Lett. 2021, 23, 8645.
[99]	Shi, Z.; Shen, C.; Dong, K. Chem.-Eur. J. 2021, 27, 18039.
[100]	Ji, L. X.; Shen, R. C.; Tian, X. X.; Zhang, R. H.; Ren, Y. X.; Dong, W. K. Angew. Chem., Int. Ed. 2022, 61, e202204156.
[101]	Liu, D.; Ru, T.; Deng, Z.; Zhang, L.; Ning, Y.; Chen, F. E. ACS Catal. 2023, 13, 12868.
[102]	Wu, X. F.; Neumanna, H.; Beller, M. Chem. Soc. Rev. 2011, 40, 4986.
[103]	Barnard, C. F. J. Organometallics 2008, 27, 5402.
[104]	Boscá, F.; Miranda, M. A. J. Photochem. Photobiol., B 1998, 43, 1.
[105]	Ong, A. L.; Kamaruddin, A. H.; Bhatia, S. Process Biochem. 2005, 40, 3526.
[106]	Zhu, Z.; Zhang, W.; Gao, Z. Prog. Chem. 2016, 28, 1626 (in Chinese).
	(朱壮丽, 张伟强, 高子伟, 化学进展, 2016, 28, 1626.)
[107]	Wu, Y.; Zeng, L.; Li, H. R.; Cao, Y.; Hu, J. C.; Xu, M. H.; Shi, R. Y.; Yi, H.; Lei, A. W. J. Am. Chem. Soc. 2021, 143, 12460.
[108]	Song, J.; Sun, H. S.; Sun, W.; Fan, Y. X.; Li, C.; Wang, H. T.; Xiao, K.; Qian, Y. Adv Synth Catal. 2019, 361, 5521.
[109]	Liu, J. H.; Chen, J.; Sun, W.; Xia, C. G. Chin. J Catal. 2010, 31, 1. (in Chinese).
	(刘建华, 陈静, 孙伟, 夏春谷, 催化学报, 2010, 31, 1.)
[110]	Bhattacherjee, D.; Rahman, M.; Ghosh, S.; Bagdi, A. K.; Zyryanov, G. V.; Chupakhin, O. N.; Das, P.; Hajra, A. Adv. Synth. Catal. 2021, 363, 1597.
[111]	Wakita, Y.; Yasunaga, T.; Akita, M.; Kojima, M. J. Organomet. Chem. 1986, 301, C17.
[112]	Ishiyama, T.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1991, 64, 1999.
[113]	Ishiyama, T.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1991, 32, 6923.
[114]	Ishiyama, T.; Kizaki, H.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1993, 34, 7595.
[115]	Couve-Bonnaire, S.; Carpentier, J. F.; Mortreux, A.; Castanet, Y. Tetrahedron 2003, 59, 2793.
[116]	Prediger, P.; Moro, A. V.; Nogueira, C. W.; Savegnago, L.; Menezes, P. H.; Rocha, J. B. T.; Zeni, G. J. Org. Chem. 2006, 71, 3786.
[117]	Zheng, S.; Xu, L.; Xia, C. Appl. Organomet. Chem. 2007, 21, 772.
[118]	Neumann, H.; Brennfuhrer, A.; Beller, M. Chem.-Eur. J. 2008, 14, 3645.
[119]	Wu, X. F.; Neumann, H.; Beller, M. Tetrahedron Lett. 2010, 51, 6146.
[120]	Wu, X. F.; Neumann, H.; Beller, M. Adv. Synth. Catal. 2011, 353, 788.
[121]	Hao, Y.; Jiang, J.; Wang, Y.; Jin, Z. Catal. Commun. 2015, 71, 106.
[122]	Gautam, P.; Tiwari, N. J.; Bhanage, B. M. ACS Omega 2019, 4, 1560.
[123]	Boubakri, L.; Al-Ayed, A. S.; Mansour, L.; Harrath, A. A.; Al-Tamimi, J.; Özdemir, I.; Yasar, S.; Hamdi, N. Transition Met. Chem. 2019, 44, 321.
[124]	Mohanty, A.; Nayak, M. K.; Roy, S. Org. Biomol. Chem. 2023, 21, 5601.
[125]	Cai, M.; Peng, J.; Hao, W.; Ding, G. Green Chem. 2011, 13, 190.
[126]	Qureshi, Z. S.; Deshmukh, K. M.; Tambade, P. J.; Bhanage, B. M. Synthesis 2011, 2011, 243.
[127]	Niu, J. R.; Huo, X.; Zhang, F. W.; Wang, H. B.; Zhao, P.; Hu, W. Q.; Ma, J.; Li, R. ChemCatChem 2013, 5, 349.
[128]	Kang, S. K.; Yamaguchi, T.; Kim, T. H.; Ho, P. S. J. Org. Chem. 1996, 61, 9082.
[129]	Zhong, Y. Z.; Han, W. Chem. Commun. 2014, 50, 3874.
[130]	Jafarpour, F.; Rashidi-Ranjbar, P.; Kashani, A. O. Eur. J. Org. Chem. 2011, 2011, 2128.
[131]	Ang, W. J.; Lo, L. C.; Lam, Y. Tetrahedron 2014, 70, 8545.
[132]	Zhang, B.; Deng, W.; Xu, Z. Y. Organometallics 2015, 42, 5882.
[133]	Talukdar, K.; Sarkar, T.; Roya, S.; Punniyamurthy, T. Chem. Commun. 2021, 57, 3359.
[134]	Li, H. L.; Yang, M.; Qi, Y. X.; Xue, J. J. Eur. J. Org. Chem. 2011, 2011, 2662.
[135]	Zhou, Q.; Wei, S. H.; Han, W. J. Org. Chem. 2014, 79, 1454.
[136]	Wu, X. F.; Neumann, H.; Spannenberg, A.; Schulz, T.; Jiao, H. J.; Beller, M. J. Am. Chem. Soc. 2010, 132, 14596.
[137]	Trzeciak, A. M.; Ziółkowski, J. J. Coord. Chem. Rev. 2005, 249, 2308.
[138]	Bloome, K. S.; Alexanian, E. J. J. Am. Chem. Soc. 2010, 132, 12823.
[139]	Gøgsig, T. M.; Nielsen, D. U.; Lindhardt, A. T.; Skrydstrup, T. Org. Lett. 2012, 14, 2536.
[140]	Wang, M. M.; Lu, S. M.; Li, C. ACS Catal. 2022, 12, 10801.
[141]	Chen, M.; Wang, X.; Yang, P.; Kou, X.; Ren, Z. H.; Guan, Z. H. Angew. Chem., Int. Ed. 2020, 59, 12199.
[142]	Sen, A.; Lai, T.-W. J. Am. Chem. Soc. 1982, 104, 3520.
[143]	Negishi, E.-I.; Miller, J. A. J. Am. Chem. Soc. 1983, 105, 6761.
[144]	Negishi, E.-I.; Tour, J. M. Tetrahedron Lett. 1986, 27, 4869.
[145]	Satoh, T.; Itaya, T.; Okuro, K.; Miura, M.; Nomura, M. J. Org. Chem. 1995, 60, 7267.
[146]	Gagnier, S. V.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 4804.
[147]	Wu, X.; Nilsson, P.; Larhed, M. J. Org. Chem. 2005, 70, 346.
[148]	Wu, X. F.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 5284.
[149]	Yin, H.; Nielsen, D. U.; Johansen, M. K.; Lindhardt, A. T.; Skry- dstrup, T. ACS Catal. 2016, 6, 2982.
[150]	Darbem, M. P.; Esteves, H. A.; Oliveira, I. M.; Stefani, H. A. Eur. J. Org. Chem. 2020, 2020, 5220.
[151]	Xu, Z. S.; Shen, C. R.; Zhang, H. R.; Wang, P.; Dong, K. W. Org. Chem. Front. 2021, 8, 1163.
[152]	Carmona, R. C.; Koster, O. D.; Correia, C. R. D. Angew. Chem., Int. Ed. 2018, 57, 2067.
[153]	Zhang, Y. D.; Chen, M.; Li, Y.; Liu, B. W.; Ren, Z. H.; Guan, Z. H. Org. Lett. 2023, 25, 8110.
[154]	Meerifield, J. H.; Godschal, J. P.; Stille, J. K. Organometallics 1984, 3, 1108.
[155]	Sheffy, F. K.; Godschalx, J. P.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4833.
[156]	Baillargeon, V. P.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 452.
[157]	Stille, J. K. Angew. Chem. 1986, 98, 504.
[158]	Sun, J.; Feng, X.; Zhao, Z.; Yamamoto, Y.; Bao, M. Tetrahedron 2014, 70, 7166.
[159]	Slobbe, P.; Windhorst, A. D.; Adamzek, K.; Bolijn, M.; Schuit, R. C.; Heideman, D. A. M.; Dongen, G. A. M. S.; Poot, A. J. Oncotarget 2017, 8, 38337.
[160]	Jin, Y.; Hok, S.; Bacsa, J.; Dai, M. J. Am. Chem. Soc. 2024, 146, 1825.
[161]	Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
[162]	Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1993, 115, 9293.
[163]	Jeanneret, V.; Meerpoel, L.; Vogel, P. Tetrahedron Lett. 1997, 38, 543.
[164]	Morera, E.; Ortar, G. Bioorg. Med. Chem. Lett. 2000, 10, 1815.
[165]	Liu, L.; Song, H.; Chen, P.; Yuan, Z.; Feng, S.; Zhang, W.; Fang, B.; Xie, X.; She, X. Org. Chem. Front. 2018, 5, 3013.
[166]	Cui, C.; Dai, M. Chin. J. Chem. 2023, 41, 3019.
[167]	Iranpoor, N.; Firouzabadi, H.; Etemadi-Davan, E. J. Organomet. Chem. 2015, 794, 282.
[168]	Tamaru, Y.; Ochiai, H.; Yamada, Y.; Yoshida, Z.-I. Tetrahedron Lett. 1983, 24, 3869.
[169]	Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 1365.
[170]	Jackson, R. F. W.; Turner, D.; Block, M. H. J. Chem. Soc., Perkin Trans. 1997, 865.
[171]	Andersen, T. L.; Donslund, A. S.; Neumann, K. T.; Skrydstrup, T. Angew. Chem., Int. Ed. 2018, 57, 800.
[172]	Weng, Y.; Zhang, C.; Tang, Z.; Shrestha, M.; Huang, W.; Qu, J.; Chen, Y. Nat. Commun. 2020, 11, 392.
[173]	Zhang, Y.; Cao, Q.; Xi, Y.; Wu, X.; Qu, J.; Chen, Y. J. Am. Chem. Soc. 2024, 146, 7971.
[174]	Wu, X. Q.; Wang, C. L.; Liu, N.; Qu, J. P.; Chen, Y. F. Nat. Commun. 2023, 14, 6960.
[175]	Huang, W. Y.; Wang, C. L.; Zhang, Y. T.; Qu, J. P.; Chen, Y. F. Org. Biomol. Chem. 2024, 22, 2380.
[176]	Kobayashi, T.; Tanaka, M. J. Chem. Soc., hem. Commun. 1981, 7, 333.
[177]	Delaude, L.; Masdeu, A. M.; Alper, H. Synthesis 1994, 1994, 1149.
[178]	Arcadi, A.; Cacchi, S.; Marinelli, F.; Pace, P.; Sanzi, G. Synlett 1995, 823.
[179]	Ahmed, M. M. S.; Mori, A. Org. Lett. 2003, 5, 3057.
[180]	Liang, B.; Huang, M.; You, Z.; Xiong, Z.; Lu, K.; Fathi, R.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 6097.
[181]	Ma, W.; Li, X.; Yang, J.; Liu, Z.; Chen, B.; Pan, X. Synthesis 2006, 2006, 2489.
[182]	Fukuyama, T.; Yamaura, R.; Ryu, I. Can. J. Chem. 2005, 83, 711.
[183]	Rahman, M. T.; Fukuyama, T.; Kamata, N.; Sato, M.; Ryu, I. Chem. Commun. 2006, 2236.
[184]	Sans, V.; Trzeciak, A. M.; Luis, S.; Ziókowski, J. Catal. Lett. 2006, 109, 37.
[185]	Liu, J. H.; Chen, J.; Xia, C. G. J. Catal. 2008, 253, 50.
[186]	Liu, J. M.; Peng, X. G.; Sun, W.; Zhao, Y. W.; Xia, C. G. Org. Lett. 2008, 10, 3933.
[187]	Tu, Y.; Zhang, Z.; Wang, T.; Ke, J.; Zhao, J. Org. Lett. 2017, 19, 3466.
[188]	Charugandla, R.; Vangala, M. S.; Chidara, S.; Babu, K. R. Tetrahedron Lett. 2018, 59, 3283.
[189]	Mansour, W.; Suleiman, R.; Fettouhi, M.; Ali, B. E. ACS Omega 2020, 5, 23687.
[190]	Xiong, W.; Wu, B.; Zhu, B.; Tan, X.; Wang, L.; Wu, W.; Qi, C.; Jiang, H. ChemCatChem 2021, 13, 2843.
[191]	Sheng, H. Y.; Chen, Z. W; Song, Q. L. J. Am. Chem. Soc. 2024, 146, 1722.
[192]	Yang, D.; Wang, D.; Liu, H.; Zhao, X.; Lu, Y.; Lai, S.; Liu, Y. Chin. J. Catal. 2016, 37, 405.
[193]	Wu, Y.; Zeng, L.; Li, H.; Cao, Y.; Hu, J.; Xu, M.; Shi, R.; Yi, H.; Lei, A. J. Am. Chem. Soc. 2021, 143, 12460.
[194]	Zhang, K.; Yao, Y.; Sun, W.; Wen, R.; Wang, Y.; Sun, H.; Zhang, W.; Zhang, G.; Gao, Z. Chem. Commun. 2021, 57, 13020.
[195]	Li, L.; Liu, X. L.; Qi, Z.; Yang, A. H.; Ma, A. J.; Peng, J. B. Org. Lett. 2022, 24, 1201.
[196]	Alper, H. J. Chem. Soc.,Chem. Commun. 1983, 1270.
[197]	Alper, H.; Hamel, N. J. Am. Chem. Soc. 1990, 112, 2803.
[198]	Alper, H. J. Org. Chem. 1992, 57, 3328.
[199]	Piotti, M. E.; Alper, H. J. Am. Chem. Soc. 1996, 118, 111.
[200]	Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484.
[201]	Zheng, Z.; Alper, H. Org. Lett. 2008, 10, 4903.
[202]	Grigg, R.; MacLachlan, W. S.; MacPherson, D. T.; Sridharan, V.; Suganthan, S.; Pett, M. T.; Zhang, J. Tetrahedron 2000, 56, 6585.
[203]	Orito, K.; Miyazawa, M.; Kanbayashi, R.; Tokuda, M.; Suginome, H. J. Org. Chem. 1999, 64, 6583.
[204]	Hassner, A. Organic Syntheses Based on Name Reactions, 3rd ed., Elsevier, Oxford, UK, 2012, pp. 8-9.
[205]	Lu, S. M.; Alper, H. J. Am. Chem. Soc. 2005, 127, 14776.
[206]	Laursen, S. R.; Jensen, M. T.; Lindhardt, A. T.; Jacobsen, M. F.; Skrydstrup, T. Eur. J. Org. Chem. 2016, 2016, 1881.
[207]	Chen, L. P.; Chen, J. F.; Zhang, Y. J.; He, X. Y.; Han, Y. F.; Xiao, Y. T.; Lv, G. F.; Lu, X.; Teng, F.; Sun, Q.; Li, J. H. Org. Chem. Front. 2021, 8, 6067.
[208]	Vangrunderbeeck, S.; Balcaen, T.; Veryser, C.; Steurs, G.; De Borg- graeve, W. M. Eur. J. Org. Chem. 2022, 2022, e202101136.
[209]	Jeong, N. In Comprehensive Organic Synthesis II, Eds.: Knochel, P.; Molander, B. A., Elsevier, Amsterdam, 2014, p. 1106.
[210]	Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Perkin Trans. 1 1973, 975.
[211]	Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
[212]	Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
[213]	Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
[214]	Belanger, D. B.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7641.
[215]	Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
[216]	Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
[217]	Itami, K.; Mitsudo, K.; Yoshida, J. I. Angew. Chem., Int. Ed. 2002, 41, 3481.
[218]	Jeong, N. Organometallics 1998, 17, 3642.
[219]	Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73.
[220]	Chahdoura, F.; Dubrulle, L.; Fourmy, K.; Durand, J.; Madec, D.; Gómez, M. Eur. J. Inorg. Chem. 2013, 2013, 5138.
[221]	Trauner, D.; Ji, X. Synfacts 2024, 20, 0419.
[222]	Oestreich, M.; Klare, H. F. T.; Brösamlen, D. Synfacts 2023, 19, 0782.
[223]	Gais, H. J. Eur. J. Org. Chem. 2024, 27, e2023011.
[224]	Wang, H.; Liu, Y.; Zhang, H.; Yang, B.; He, H.; Gao, S. J. Am. Chem. Soc. 2023, 145, 16988.
[225]	Yang, Z. Acc. Chem. Res. 2021, 54, 556.
[226]	Roglans, A.; Pla-Quintana, A.; Solà, M. Chem. Rev. 2021, 121, 1894.
[227]	Lledóa, A.; Solàb, J. Adv. Synth. Catal. 2024, 366, 574.
[228]	Zou, Y. P.; Lai, Z. L.; Zhang, M. W.; Peng, J.; Ning, S.; Li, C. C. J. Am. Chem. Soc. 2023, 145, 10998.
[229]	Wang, Y. Q.; Xu, K.; Min, L.; Li, C. C. J. Am. Chem. Soc. 2022, 144, 10162.
[230]	Asano, S.; Nakama, K. I.; Arimoto, H. Tetrahedron Lett. 2020, 61, 151974.
[231]	Yang, P.; Zhang, Y.; Chen, M.; Zhao, Q.; Ren, Z. H.; Guan, Z. H. Org. Lett. 2021, 23, 9241.
[232]	Shyshkanov, S.; Vasilyev, D. V.; Abhyankar, K. A.; Stylianou, K. C.; Dyson, P. J. Eur. J. Inorg. Chem. 2022, 2022, e202200037.
[233]	Teng, Q.; Chen, D.; Tung, C. H.; Xu, Z. Org. Chem. Front. 2022, 9, 1680.
[234]	Huang, H. G.; Zheng, Y. Q.; Zhong, D.; Deng, J. L.; Liu, W. B. J. Am. Chem. Soc. 2023, 145, 10463.
[235]	Li, J. J. Name Reactions: A Collection of Detailed Reaction Mechanisms, 2nd ed., 2003, Springer Berlin, Heidelberg, p. 157.
[236]	Gattermann, L.; Berchelmann, W. Ber. Dtsch. Chem. Ges. 1898, 31, 1765.
[237]	Doana, M. I.; Ciuculescu, A.; Bruckner, A.; Pop, M.; Filip, P. Rev. Roum. Chim. 2001, 46, 345.
[238]	Gilani, S. Z. A.; Lu, L.; Arslan, M. T.; Ali, B.; Wang, Q.; Wei, F. Catal. Sci. Technol. 2020, 10, 3366.
[239]	Benington, F.; Morin, R. D.; Clark, L. C. J. Org. Chem. 1954, 19, 11.
[240]	Toniolo, L. J. Organomet. Chem. 1980, 194, 221.
[241]	Tanaka, M.; Souma, Y. J. Chem. Soc., Chem. Commun. 1991, 1551.
[242]	Tanaka, M.; Iyoda, J.; Souma, Y. J. Org. Chem. 1992, 57, 2677.
[243]	Tanaka, M.; Souma, Y. J. Org. Chem. 1992, 57, 3738.
[244]	Tanaka, M.; Fujiwara, M.; Ando, H.; Souma, Y. J. Org. Chem. 1993, 58, 3213.
[245]	Tanaka, M.; Fujiwara, M.; Ando, H. J. Org. Chem. 1995, 60, 2106.
[246]	Tanaka, M.; Fujiwara, M.; Xu, Q.; Souma, Y.; Ando, H.; Laali, K. K. J. Am. Chem. Soc. 1997, 119, 5100.
[247]	Tanaka, M.; Fujiwara, M.; Xu, Q.; Ando, H.; Raeker, T. J. J. Org. Chem. 1998, 63, 4408.
[248]	Omann, L.; Qu, Z. W.; Irran, E.; Klare, H. F. T.; Grimme, S.; Oestreich, M. Angew. Chem., Int. Ed. 2018, 57, 8301.
[249]	Koch, H.; Haaf, W. Liebig’s Ann. 1958, 618, 251.
[250]	Hiraoka, K.; Kebarle, P. J. Am. Chem. Soc. 1977, 99, 366.
[251]	Langhals, H.; Mergelsberg, I.; Rüchardt, C. Tetrahedron Lett. 1981, 22, 2365.
[252]	Takahashi, Y.; Yoneda, N. Synth. Commun. 1989, 19, 1945.
[253]	Stepanov, A. G.; Luzgin, M. V.; Romannikov, V. N.; Zamaraev, K. I. J. Am. Chem. Soc. 1995, 117, 3615.
[254]	Olah, G. A.; Prakash, G. K. S.; Mathew, T.; Marinez, E. R. Angew. Chem., Int. Ed. 2000, 39, 2547.
[255]	Emert, J. I.; Dankworth, D. C.; Gutierrez, A. Macromol 2001, 34, 2766.
[256]	Li, T.; Tsumori, N.; Souma, Y.; Xu, Q. Chem. Commun. 2003, 2070.
[257]	Davis, M. C.; Liu, S. Synth. Commun. 2006, 36, 3509.
[258]	Kozhushkov, S. I.; Yufit, D. S.; Boese, R.; Bläser, D.; Schreiner, P. R.; Meijere, A. Eur. J. Org. Chem. 2005, 2005, 1409.
[259]	Li, J. J. Name Reactions-A Collection of Detailed Reaction Mechanisms, Springer Berlin, Heidelberg, 2008, p. 349.
[260]	Wanka, L.; Cabrele, C.; Vanejews, M.; Schreiner, P. R. Eur. J. Org. Chem. 2007, 2007, 1474.
[261]	Cai, Q.-L.; Peng, S.-Y. Catalytic Action in C1 Chemistry, Chemical Indurstry Press, Beijing, 1995, p. 473 (in Chinese).
	(蔡启璃, 彭少逸编著, 化学工业出版社, 北京, 碳一化学中的催化作用, 1995, p. 473.)
[262]	Aronson, M. T.; Gorte, R. J.; Farneth, W. E. J. Catal. 1987, 105, 455.
[263]	Aronson, M. T.; Gorte, R. J.; Farneth, W. E.; White, D. J. Am. Chem. Soc. 1989, 111, 840.
[264]	Pavlov, D. I.; Sukhikh, T. S.; Potapov, A. S. Russ. Chem. Bull., Int. Ed. 2020, 69, 1953.
[265]	Ivlevaa, E. A.; Khamzina, M. R.; Zaborskaya, M. S.; Klimochkin, Y. N. Russ. J. Org. Chem. 2022, 58, 982.
[266]	Ivlevaa, E. A.; Simatova, E. V.; Zaborskaya, M. S.; Kazachkova, M. S.; Rybakov, V. B.; Klimochkin, Y. N. Russ. J. Org. Chem. 2023, 59, 409.
[267]	Semmelhack, M. F.; Bodurow, C. J. Am. Chem. Soc. 1984, 106, 1496.
[268]	Semmelhack, M. F.; Kim, C.; Zhang, N.; Bodurow, C.; Sanner, M.; Dobler, W.; Meier, M. Pure Appl. Chem. 1990, 62, 2035.
[269]	Ma, K.; Martin, B. S.; Yin, X.; Dai, M. Nat. Prod. Rep. 2019, 36, 174.
[270]	Wahl, K. J. L.; Winger, B. E.; Smith, R. D. J. Am. Chem. Soc. 1993, 115, 5869.
[271]	Kraus, G. A.; Li, J. J. Am. Chem. Soc. 1993, 115, 5859.
[272]	White, J. D.; Kranemann, C. L.; Kuntiyong, P. Org. Lett. 2001, 3, 4003.
[273]	Hayes, P. Y.; Kitching, W. J. Am. Chem. Soc. 2002, 124, 9718.
[274]	Xu, X. S.; Li, Z. W.; Zhang, Y. J.; Peng, X. S.; Wong, H. N. C. Chem. Commun. 2012, 48, 8517.
[275]	Hornberger, K. R.; Hamblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894.
[276]	Carpenter, J.; Northrup, A. B.; Chung, D.; Wiener, J. J. M.; Kim, S. G.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2008, 47, 3568.
[277]	Marshall, J. A.; Yanik, M. M. Tetrahedron Lett. 2000, 41, 4717.
[278]	Tietze, L. F.; Fischer, R.; Guder, H. J.; Goerlach, A.; Meumann, M.; Krach, T. Carbohydr. Res. 1987, 164, 177.
[279]	Tietze, L. F.; Spiegl, D. A.; Stecker, F.; Major, J.; Raith, C.; Große, C. Chem.-Eur. J. 2008, 14, 8956.
[280]	Yang, Z.; Zhang, B.; Zhao, G.; Yang, J.; Xie, X.; She, X. Org. Lett. 2011, 13, 5916.
[281]	Lu, Y.; Kim, I. S.; Hassan, A.; Valle, D. J. D.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 5018.
[282]	Han, S. B.; Hassan, A.; Kim, I. S.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 15559.
[283]	Werness, J. B.; Tang, W. Org. Lett. 2011, 13, 3664.
[284]	Ebner, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 11227.
[285]	Ojima, I. J. Mol. Catal. 1986, 37, 25.
[286]	Ojima, I. Chem. Rev. 1988, 88, 1011.
[287]	Beller, M.; Eckert, M. Angew. Chem., Int. Ed. 2000, 39, 1010.
[288]	Beller, M.; Eckert, M.; Vollmuller, F.; Bogdanovic, S.; Geissler, H. Angew. Chem. Int. Ed. Engl. 1997, 36, 1494.
[289]	Beller, M.; Moradi, W. A.; Eckert, M.; Neumann, H. Tetrahedron Lett. 1999, 40, 4523.
[290]	Akiyama, R.; Sagae, T.; Sugiura, M.; Kobayashi, S. J. Organomet. Chem. 2004, 689, 3806.
[291]	Yang, K. W.; Jiang, X. Z. Bull. Chem. Soc. Jpn. 2006, 79, 806.
[292]	Wakamatsu, H.; Uda, J.; Yamakami, N. J. Chem. Soc., Chem. Commun. 1971, 1540.
[293]	Parnaud, J. J.; Campari, G.; Pino, P. J. Mol. Catal. 1979, 6, 341.
[294]	Magnus, P.; Slater, M. Tetrahedron Lett. 1987, 28, 2829.
[295]	Stern, R.; Reffet, D.; Hirschauer, A.; Commereuc, D.; Chauvin, Y. Synth. Commun. 1982, 12, 1111.
[296]	Wang, F.; Zhang, Z. G. Chin. J. Org. Chem. 2002, 22, 536 (in Chinese).
	(王峰, 张兆国, 有机化学, 2002, 22, 536.)
[297]	Izawa, K. J. Synth. Org. Chem. 1988, 46, 218.
[298]	Ojima, J.; Zhang, Z. Organometallics 1990, 9, 3122.
[299]	Yuan, S. S.; Ajami, A. M. J. Organomet. Chem. 1986, 302, 255.
[300]	Beller, M.; Eckert, M.; Holla, E. W. J. Org. Chem. 1998, 63, 5658.
[301]	Ogawa, H.; Yang, Z. K.; Minami, H.; Kojima, K.; Saito, T.; Wang, C.; Uchiyama, M. ACS Catal. 2017, 7, 3988.
[302]	Li, Q. H.; Luo, R. Q.; Wu, C.; Xiao, H. L.; Guo, S. P.; Zhang, Z. H.; Huang, Z. Y.; Zhou, L. Chin. J. Org. Chem. 2021, 41, 1489 (in Chinese).
	(李清寒, 罗瑞强, 吴川, 肖红柳, 郭少鹏, 张志豪, 黄哲耀, 周林, 有机化学, 2021, 41, 1489.)
[303]	Wang, C. L.; Wu, X. Q.; Li, H. Y.; Qu, J. P.; Chen, Y. F. Angew. Chem., Int. Ed. 2022, 61, e202210484.
[304]	Su, L.; Gao, S.; Liu, J. W. Nat. Commun. 2024, 15, 7248.
[305]	Yuan, Y.; Zhang, Y. C.; Wu, X. F. Nat. Commun. 2024, 15, 6705.
[306]	Wang, Z.; Shen, C. R.; Dong, K. W. Angew. Chem., Int. Ed. 2024, 63, e202410967.