多取代烯烃的Z∶E高选择性合成制备

doi:10.6023/cjoc202212039

摘要/Abstract

烯烃是工业生产和药物合成中最常见的原料之一, 关于烯烃制备方法的报道层出不穷. 由于Z-构型烯烃与E-构型烯烃在理化性质和生物活性等方面存在很大的差异, 所以烯烃结构的Z∶E构型控制是合成方法学的热点之一. 综述了烯烃的立体选择性合成方法, 着重总结了双取代内烯烃和三取代烯烃的Z∶E构型的选择性制备. 以Z∶E选择性为主要分类标准, 解读了Wittig反应、取代烷烃消除反应、烯烃异构化反应、烯烃复分解反应、烯烃偶联反应、炔烃加成反应的相关报道, 并比较详细地描述了这些合成方法中的催化剂种类和Z∶E选择性的控制因素.

关键词: 双取代内烯烃, 三取代烯烃, Z∶E选择性

Olefin is one of the most important bulk chemicals in industry as well as commonly used starting materials in pharmaceutical field. Since Z-olefins and E-olefins exhibit great differences in physicochemical properties and biological activities, the Z∶E configuration control has been playing important roles in olefin preparation. The selective synthetic methods of Z∶E configurations of disubstituted inner alkenes and trisubstituted alkenes are reviewed, including the Wittig reaction, substituted alkane elimination reaction, olefin isomerization reaction, olefin metathesis, olefin coupling reaction, and alkyne addition reaction. The catalyst types and controlling factors of Z∶E selectivity in these synthetic examples are described in detail.

Key words: disubstituted internal olefins, trisubstituted olefins, Z∶E selectivity

引用此文

郭萍, 周勇, 赵杰. 多取代烯烃的Z∶E高选择性合成制备[J]. 有机化学, 2023, 43(3): 855-872.

Ping Guo, Yong Zhou, Jie Zhao. Z∶E Selective Preparation of Disubstituted Internal Alkenes and Trisubstituted Alkenes[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 855-872.

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图/表 64

图式1. 钌催化重氮化合物与硫叶立德的交叉烯烃反应

Scheme 1. Ruthenium-catalyzed cross-olefination of diazo compounds with sulfoxonium ylides Reproduced from Ref. [31] with permission from John Wiley and Sons

图式2. TrBF4催化的α-烷基重氮酯选择性生成Z-α,β-不饱和酯的反应和可能的机理

Scheme 2. Reaction and possible mechanism of selective formation of Z-α,β-unsaturated esters by α-alkyl diazo esters catalyzed by TrBF4 Reproduced from Ref. [32] with permission from the Royal Society of Chemistry

图式3. 光催化烯烃的构型转化

Scheme 3. Photocatalytic configuration transformation of olefin Reproduced from Ref. [33] with permission from the Royal Society of Chemistry

图式4. 二苯乙烯光氧化还原异构化催化剂在离子液体中的固定化研究

Scheme 4. Immobilization of the photoredox catalyst in ionic liquid for the photoredox isomerization of stilbene Reproduced from Ref. [34] with permission from John Wiley and Sons

图式5. 钌化合物催化的高Z-选择性和对映选择性开环/交叉复分解反应

Scheme 5. Ru complex catalyzed high Z-selectivity and enantioselectivity ring-open/cross metathesis reaction Reproduced from Ref. [37] with permission from the American Chemical Society

图式6. 钼化合物催化的烯烃复分解反应得到三氟甲基取代的烯烃

Scheme 6. Mo compound catalyzed olefin metathesis reactions to obtain trifluoromethyl-substituted olefin Reproduced from Ref. [39] with permission from Springer Nature

图式7. 钌催化的炔烃选择性半加氢反应

Scheme 7. Selective semi-hydrogenation of alkynes catalyzed by ruthenium Reproduced from Ref. [40] with permission from the American Chemical Society

图式8. 无负载纳米多孔钯催化剂催化炔烃半加氢反应机理

Scheme 8. Mechanism of semi-hydrogenation of alkynes catalyzed by an unsupported nanoporous palladium catalyst Reproduced from Ref. [41] with permission from the American Chemical Society

图式9. 异相钯催化炔烃选择性半氢化制备Z-烯烃

Scheme 9. Preparation of cis-alkenes by selective semi-hydro- genation of heterogeneous palladium-catalyzed alkynes Reproduced from Ref. [42] with permission from the American Chemical Society

图式10. 钯催化的配体调控炔烃的选择性氢化反应

Scheme 10. Palladium-catalyzed ligand regulating selective hydrogenation of alkynes Reproduced from Ref. [43] with permission from John Wiley and Sons

图式11. 钯催化的炔烃还原偶联反应

Scheme 11. Palladium-catalyzed alkyne reduction coupling reaction Reproduced from Ref. [44] with permission from John Wiley and Sons

图式12. 镍催化的炔烃选择性半氢化反应

Scheme 12. Nickel catalyzed selective semi-hydrogenation of alkynes Reproduced from Ref. [45] with permission from John Wiley and Sons

图式13. 铜催化的炔烃选择性氢烷基化反应

Scheme 13. Copper catalyzed selective hydroalkylation of alkynes Reproduced from Ref. [46] with permission from the American Chemical Society

图式14. 银催化的炔烃的氢烷基化反应可能的反应机理

Scheme 14. Possible mechanism of hydrogenalkylation of alkynes catalyzed by silver Reproduced from Ref. [48] with permission from the American Chemical Society

图式15. 苯乙酸直接脱羧消除制备烯烃

Scheme 15. Preparation of olefin by direct decarboxylation of phenylacetic acid Reproduced from Ref. [49] with permission from the American Chemical Society

图式16. 铁催化的甲基取代N-杂芳烃与伯醇发生α-烯化反应

Scheme 16. Fe-catalyzed α-olefination of methyl-substituted N-heteroarenes with primary alcohols Reproduced from Ref. [51] with permission from the American Chemical Society

图式17. 电子给体-受体反应脱羰基策略

Scheme 17. Decarbonylation strategies for electron donor-acce- ptor reactions Reproduced from Ref. [52] with permission from the Royal Society of Chemistry

图式18. 肼介导的镍催化酮的立体选择性烯化反应

Scheme 18. Nickel-catalyzed stereoselective alkenylation of ketones mediated by hydrazine Reproduced from Ref. [53] with permission from the American Chemical Society

图式19. 钴催化的β-取代苯乙烯Z-E异构化反应

Scheme 19. Cobalt-catalyzed Z to E isomerization of β-substi- tuted styrenes Reproduced from Ref. [54] with permission from the American Chemical Society

图式20. 铱催化的构型单一的1-烯烃异构化生成E-2-烯烃

Scheme 20. Iridium catalyzed monoisomerization of 1-alkenes to trans-2-alkenes Reproduced from Ref. [55] with permission from John Wiley and Sons

图式21. 可见光-钴催化烯烃选择性异构化

Scheme 21. Visible-light-cobalt catalyzed selective isomerization of olefin Reproduced from Ref. [56] with permission from John Wiley and Sons

图式22. (Ni)(I)-催化分子内1,3-氢原子迁移

Scheme 22. (Ni)(I)-catalyzed intramolecular 1,3-hydrogen atom relocation Reproduced from Ref. [57] with permission from the American Association for the Advancement of Science

图式23. Mn(I)钳形配合物通过N—H协同作用催化烯烃位移的转换

Scheme 23. Mn(I) pincer complexes catalyzed olefin transposition via N—H cooperativity Reproduced from Ref. [58] with permission from the American Chemical Society

图式24. 膦酰膦酸酯促进的醛的交叉偶联反应

Scheme 24. Cross-coupling of aldehydes facilitated by phosphonyl phosphonate esters Reproduced from Ref. [59] with permission from the American Chemical Society

图式25. 锰催化的醇与肼/腙脱氢偶联直接转化烯烃

Scheme 25. Manganese catalyzed dehydrogenation of alcohol to hydrazine/hydrazone directly to alkenes Reproduced from Ref. [60] with permission from John Wiley and Sons

图式26. 镍催化的芳基烯烃与醛的脱氢Heck偶联反应

Scheme 26. Direct dehydrogenative alkyl Heck-couplings of aryl alkenes with aldehydes catalyzed by nickel Reproduced from Ref. [61] with permission from Springer Nature

图式27. Heck氧化反应式和POP-9结构图

Scheme 27. Oxidative Heck reactions and ligands structure of POP-9 Reproduced from Ref. [62] with permission from John Wiley and Sons

图式28. 2-溴酚催化的烯烃与氟烷基碘化物的Heck偶联反应

Scheme 28. 2-Bromophenol catalyzed Heck coupling reaction of alkenes with fluoroalkyl iodide Reproduced from Ref. [63] with permission from the Royal Society of Chemistry

图式29. 铑催化的酮与B2pin2发生的脱氧和硼化反应

Scheme 29. Rhodium-catalyzed deoxidation and boration of ketone with B2pin2 Reproduced from Ref. [64] with permission from the American Chemical Society

图式30. Cu(I)催化3-芳基苯并呋喃-2(3H)-酮叔C(sp3)—H键的C—H烯基化反应

Scheme 30. Cu(I)-catalyzed C—H alkenylation of tertiary C(sp3)—H bonds of 3?aryl benzofuran-2(3H)?ones Reproduced from Ref. [46] with permission from the American Chemical Society

图式31. 钼催化的烯烃的复分解反应选择性制备卤代烯烃

Scheme 31. Molybdenum-catalyzed selective preparation of halogenated olefin by olefin metathesis reaction Reproduced from Ref. [65] with permission from American Association for the Advancement of Science

图式32. 聚乙二醇介导的乙烯基硼酸盐与烯烃的可循环硼化偶联

Scheme 32. PEG-mediated recyclable borylative coupling of vinyl boronates with olefins Reproduced from Ref. [66] with permission from Elsevier Inc.

图式33. 臭氧/FeII介导的脱烷基化烯烃化反应

Scheme 33. Reaction of ozone/FeII-mediated dealkenylative alkenylation Reproduced from Ref. [67] with permission from John Wiley and Sons

图式 34. Ag-Ru杂双金属催化炔烃选择性半氢化

Scheme 34. Ag-Ru heterobimetallic catalyzed selective semi- hydrogenation of alkynes Reproduced from Ref. [68] with permission from the American Chemical Society

图式35. 钌催化的炔烃的半氢化反应制备E-烯烃

Scheme 35. Ruthenium catalyzed E?selective semihydrogenation of alkynes Reproduced from Ref. [40] with permission from the American Chemical Society

图式36. Pd3Pb/SiO2和RhSb/SiO2协同催化的炔烃的一锅E-烯烃合成

Scheme 36. Pd3Pb/SiO2 and RhSb/SiO2 cocatalyzed one-pot E-olefin synthesis of alkynes Reproduced from Ref. [69] with permission from the American Chemical Society

图式37. Pd和ZnI2催化的炔烃的选择性性半氢化

Scheme 37. Pd and ZnI2 catalyzed selective semi-hydrogenation of alkynes Reproduced from Ref. [70] with permission from the American Chemical Society

图式38. 钯催化的炔烃半氢化反应

Scheme 38. Palladium-catalyzed semi-hydrogenation of alkynes Reproduced from Ref. [43] with permission from John Wiley and Sons

图式39. 膦介导的炔烃半氢化反应

Scheme 39. Phosphine-mediated semi-hydrogenation of alkynes Reproduced from Ref. [71] with permission from the Royal Society of Chemistry

图式40. 钌催化选择性炔烃半氢化反应

Scheme 40. Ru-catalyzed selective semi-hydrogenation of alkynes Reproduced from Ref. [73] with permission from the Royal Society of Chemistry

图式41. 镍催化的炔烃的半氢化反应制备E-烯烃

Scheme 41. Preparation of trans-olefin by nickel-catalyzed semi- hydrogenation of alkynes Reproduced from Ref. [45] with permission from John Wiley and Sons

图式42. 铁催化的炔烃氢硅化反应

Scheme 42. Iron catalyzed hydrosilylation of alkynes Reproduced from Ref. [74] with permission from the American Chemical Society

图式43. 膦介导的炔烃选择性还原生成E-烯烃

Scheme 43. Phosphine mediated selective reduction of alkynes to E-alkenes Reproduced from Ref. [71] with permission from the Royal Society of Chemistry

图式44. 镁催化的炔烃硼氢化机理

Scheme 44. Mechanism of magnesium catalyzed borohydrogenation of alkynes Reproduced from Ref. [75] with permission from John Wiley and Sons

图式45. 铜单原子催化剂催化的炔烃的硼氢化加成反应

Scheme 45. Copper single-atom catalyst catalyzed hydroboration addition of alkynes Reproduced from Ref. [76] with permission from Elsevier Inc.

图式46. 铜和钯催化的串联Sonogashira偶联和半还原反应

Scheme 46. Copper and palladium catalyzed series Sonogashira coupling and semi-reduction reaction Reproduced from Ref. [77] with permission from the American Chemical Society

图式47. 钯催化末端炔与芳基碘化物的还原偶联反应

Scheme 47. Palladium-catalyzed reductive coupling reaction of terminal alkynes with aryl iodides Reproduced from Ref. [78] with permission from John Wiley and Sons

图式48. 铜和镍催化的末端炔的反马氏氢烷基化反应

Scheme 48. Copper and nickel catalyzed anti-markovnikov hydroalkylation of terminal alkynes Reproduced from Ref. [79] with permission from the American Chemical Society

图式49. 铜催化的末端炔与α-溴羰基立体选择性偶联

Scheme 49. Cu-catalyzed stereoselective coupling of terminal alkynes and α-bromo carbonyls Reproduced from Ref. [80] with permission from the American Chemical Society

图式50. 苯乙烯基硼E-Z异构的光催化反应

Scheme 50. Photocatalytic E-Z isomerization of styrenyl boron species Reproduced from Ref. [81] with permission from John Wiley and Sons

图式51. 铑(I)催化硼酸和E-氟代烯烃的脱氟偶联反应

Scheme 51. Rhodium(I)-catalyzed defluorinative coupling of boronic acids with monofluoroalkenes Reproduced from Ref. [82] with permission from John Wiley and Sons

图式52. Sc(OTf)3催化的区域选择性炔烃硼氢化反应

Scheme 52. Sc(OTf)3 catalyzed regioselective hydroboration of alkynes Reproduced from Ref. [83] with permission from the Royal Society of Chemistry

图式53. 铁催化的选择性氢硅化反应

Scheme 53. Reaction of Fe-catalyzed selective hydrosilication Reproduced from Ref. [74] with permission from the American Chemical Society

图式54. 铱催化的烯烃-炔交叉偶联反应

Scheme 54. Iridium-catalyzed alkene-alkyne cross coupling reaction Reproduced from Ref. [84] with permission from the American Chemical Society

图式55. 钯催化的芳基取代炔烃与腙的形式氢烷基化反应

Scheme 55. Palladium-catalyzed formal hydroalkylation of aryl- substituted alkynes with hydrazones Reproduced from Ref. [85] with permission from John Wiley and Sons

图式56. 膦介导的醛、α-卤代羰基化合物和末端烯烃三组分体系

Scheme 57. Phosphine-mediated three-component system of aldehydes, α-halo carbonyl compounds, and terminal alkenes Reproduced from Ref. [86] with permission from John Wiley and Sons

图式57. 光氧化还原/钴双催化脱羧消除N-酰基氨基酸

Scheme 57. Decarboxylative elimination of N?acyl amino acids via photoredox/cobalt dual catalysis Reproduced from Ref. [87] with permission from the American Chemical Society

图式58. 蓝光促进芳基重氮乙酸酯和重氮羰基化合物的交叉偶联

Scheme 58. Blue light-promoted cross-coupling of aryldiazoacetates and diazocarbonyl compounds Reproduced from Ref. [88] with permission from the Royal Society of Chemistry

图式59. 钴催化炔烃溴-羧基二氟甲基化

Scheme 59. Cobalt-catalyzed bromo-carboxydifluoromethyla- tion of alkynes Reproduced from Ref. [89] with permission from the Royal Society of Chemistry

图式60. 蓝光下炔烃与二氟碘乙酸乙酯加成反应

Scheme 60. The addition of alkynes to ethyl difluoroiodoacetate under blue light Reproduced from Ref. [90] with permission from the American Chemical Society

图式61. 2-溴酚催化的炔烃加成制备烯烃

Scheme 61. 2-Bromophenol catalyzed preparation of of alkenes by addition of alkynes Reproduced from Ref. [63] with permission from the Royal Society of Chemistry

图式62. 铜催化的末端炔E-选择性1,1-二硼化反应

Scheme 62. Copper catalyzed E-selective 1,1-diboration of terminal alkynes Reproduced from Ref. [91] with permission from the American Chemical Society

图式63. 异相钯催化的炔烃的硅氢化反应

Scheme 63. Heteropalladium-catalyzed hydrosilylation of alkynes Reproduced from Ref. [92] with permission from Springer Nature

图式64. 铜催化的炔烃的双功能化反应

Scheme 64. Cu-catalyzed alkyne difunctionalization Reproduced from Ref. [93] with permission from the Chinese Chemical Society (CCS), Shanghai Institute of Organic Chemistry (SIOC), and the Royal Society of Chemistry

参考文献 93

[1]	Kyriakou, G.; Boucher, M. B.; Jewell, A. D.; Lewis, E. A.; Lawton, T J.; Baber, A. E.; Tierney, H. L.; Flytzani-Stephanopoulos, M.; H. Sykes, E. C. Science 2012, 335, 1209 doi: 10.1126/science.1215864
[2]	Pei, G. X.; Liu, X. Y.; Wang, A.; Lee, A. F.; Isaacs, M. A.; Li, L.; Pan, X.; Yang, X.; Wang, X.; Tai, Z.; Wilson, K.; Zhang, T. ACS Catal. 2015, 5, 3717. doi: 10.1021/acscatal.5b00700
[3]	Pei, G. X.; Liu, X. Y.; Yang, X.; Zhang, L.; Wang, A.; Li, L.; Wang, H.; Wang, X.; Zhang, T. ACS Catal. 2017, 7, 1491. doi: 10.1021/acscatal.6b03293
[4]	Zhou, S.; Shang, L.; Zhao, Y.; Shi, R.; Waterhouse, G. I. N.; Huang, Y. C.; Zheng, L.; Zhang, T. Adv. Mater. 2019, 31, 1900509. doi: 10.1002/adma.v31.18
[5]	Feng, Q.; Zhao, S.; Xu, Q.; Chen, W.; Tian, S.; Wang, Y.; Yan, W.; Luo, J.; Wang, D.; Li, Y. Adv. Mater. 2019, 31, 1901024. doi: 10.1002/adma.v31.36
[6]	Guo, Y.; Qi, H.; Su, Y.; Jiang, Q.; Cui, Y. T.; Li, L.; Qiao, B. Chem. Nano. Mat. 2021, 7, 526.
[7]	He, X.; He, Q.; Deng, Y.; Peng, M.; Chen, H.; Zhang, Y.; Yao, S.; Zhang, M.; Xiao, D.; Ma, D.; Ge, B.; Ji, H. Nat. Commun. 2019, 10, 3663. doi: 10.1038/s41467-019-11619-6
[8]	Liu, Y.; Guo, W.; Li, X.; Jiang, P.; Zhang, N.; Liang, M. ACS Appl. Nano. Mater. 2021, 4, 5292. doi: 10.1021/acsanm.1c00646
[9]	Zhang, X.; Lin, H.; Zhang, J.; Qiu, Y.; Zhang, Z.; Xu, Q.; Meng, G.; Yan, W.; Gu, L.; Zheng, L.; Wang, D.; Li, Y. Chem. Sci. 2021, 12, 14599. doi: 10.1039/d1sc04344g pmid: 34881012
[10]	Guo, P.; Liu, H.; Zhao, J. Nano Res. 2022, 15, 7840. doi: 10.1007/s12274-022-4495-z
[11]	Alami, M.; Hamze, A.; Provot, O. ACS Catal. 2019, 9, 3437.
[12]	Pang, X.; Peng, X.; Shu, X. Synthesis 2020, 52, 3751. doi: 10.1055/s-0040-1707342
[13]	Polák, P.; Vánˇová, H.; Dvorˇák, D.; Tobrman, T.; Tetrahedron Lett. 2016, 3684.
[14]	Buttard, F.; Sharma, J.; Champagne, P. A. Chem. Commun. 2021, 57, 4071. doi: 10.1039/D1CC00596K
[15]	Duan, X. F. Chem. Commun. 2020, 56, 14937. doi: 10.1039/D0CC04882H
[16]	Mukherjee, N.; Planer, S.; Grela, K. Org. Chem. Front. 2018, 5, 494. doi: 10.1039/C7QO00800G
[17]	Tobrman, T.; Mrkobrada, S. Organics 2022, 3, 210. doi: 10.3390/org3030017
[18]	Hu, J.; Wang, M.; Pu, X.; Shi, Z. Nat. Commun. 2017, 8, 14993. doi: 10.1038/ncomms14993
[19]	Kusumoto, S.; Tatsuki, T.; Nozaki, K. Angew. Chem., Int. Ed. 2015, 54, 8458. doi: 10.1002/anie.201503620 pmid: 26089259
[20]	Fang, X. J.; Yu, P.; Morandi, B. Science 2016, 351, 832. doi: 10.1126/science.aae0427
[21]	Bissember, A. C.; Levina, A.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 14232. doi: 10.1021/ja306323x pmid: 22905894
[22]	Chatterjee, A.; Hopen Eliasson, S. H.; Törnroos, K. W.; Jensen, V. R. ACS. Catal. 2016, 6, 7784. doi: 10.1021/acscatal.6b02460
[23]	Maetani, S.; Fukuyama, T.; Suzuki, N.; Ishihara, D.; Ryu, I. Chem. Commun. 2012, 48, 2552. doi: 10.1039/c2cc18093f
[24]	Li, Y.; Liu, D.; Wan, L.; Zhang, J. Y.; Lu, X.; Fu, Y. J. Am. Chem. Soc. 2022, 144, 13961. doi: 10.1021/jacs.2c06279
[25]	He, X.; He, Q.; Deng, Y.; Peng, M.; Chen, H.; Zhang, Y.; Yao, S.; Zhang, M.; Xiao, D.; Ma, D.; Ge, B.; Ji, H. Nat. Commun. 2019, 10, 3663. doi: 10.1038/s41467-019-11619-6
[26]	Lee, Y. H.; Morandi, B. Angew. Chem., Int. Ed. 2019, 58, 6444. doi: 10.1002/anie.v58.19
[27]	Liu, C. F.; Wang, H.; Martin, R. T.; Zhao, H.; Gutierrez, O.; Koh, M. J. Nat. Catal. 2021, 4, 674. doi: 10.1038/s41929-021-00658-2
[28]	Li, X.; He, S.; Song, Q. Org. Lett. 2021, 23, 2994. doi: 10.1021/acs.orglett.1c00669
[29]	Li, Y. T.; Shao, Q. Z.; He, H. C.; Zhu, C. J.; Xue, X. S.; Xie, J. Nat. Commun. 2022, 13, 10.
[30]	Zhao, Y. L.; Liu, C. F.; Leroy, Q. H. L.; Chan, A. S. C.; Koh, M. J. Angew. Chem., Int. Ed. 2022, 61, e202202674.
[31]	Neuhaus, J. D.; Bauer, A.; Pinto, A.; Maulide, N. Angew. Chem., Int. Ed. 2018, 57, 16215. doi: 10.1002/anie.201809934 pmid: 30264529
[32]	Shang, W.; Duan, D.; Liu, Y.; Lv, J. Org. Lett. 2019, 21, 8013. doi: 10.1021/acs.orglett.9b03005
[33]	Singh, K.; Staig, S. J.; Weaver, J. D. J. Am. Chem. Soc. 2014, 136, 5275. doi: 10.1021/ja5019749
[34]	Fabry, D. C.; Ronge, M. A.; Rueping, M. Chem.-Eur.J. 2015, 21, 5350.
[35]	Herbert, M. B.; Grubbs, R. H. Angew. Chem., Int. Ed. 2015, 54, 5018. doi: 10.1002/anie.201411588 pmid: 25802009
[36]	Keitz, B. K.; Endo, K.; Patel, P. R.; Herbert, M. B.; Grubbs, R. H. J. Am. Chem. Soc. 2012, 134, 693. doi: 10.1021/ja210225e
[37]	Hartung, J.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 10183. doi: 10.1021/ja4046422 pmid: 23822901
[38]	Rosebrugh, L. E.; Herbert, M. B.; Marx, V. M.; Keitz, B. K. J. Am. Chem. Soc. 2013, 135, 1276. doi: 10.1021/ja311916m pmid: 23317178
[39]	Koh, M. J.; Nguyen, T. T.; Lam, J. K.; Torker, S.; Hyvl, J.; Schrock, R. R.; Hoveyda, A. H. Nature 2017, 542, 80. doi: 10.1038/nature21043
[40]	Kusy, R.; Grela, K. Org. Lett. 2016, 18, 6196. doi: 10.1021/acs.orglett.6b03254
[41]	Lu, Y.; Feng, X.; Takale, B. S.; Yamamoto, Y.; Zhang, W.; Bao, M. ACS Catal. 2017, 7, 8296. doi: 10.1021/acscatal.7b02915
[42]	Iwasaki, R.; Tanaka, E.; Ichihashi, T.; Idemoto, Y.; Endo, K. J. Org. Chem. 2018, 83, 13574. doi: 10.1021/acs.joc.8b02169 pmid: 30351927
[43]	Rao, S.; Prabhu, K. R. Chem.-Eur. J. 2018, 24, 13954. doi: 10.1002/chem.201803147
[44]	Hancker, S.; Neumann, H.; Beller, M. Eur. J. Org. Chem. 2018, 5253.
[45]	Murugesan, K.; Bheeter, C. B.; Linnebank, P. R.; Spannenberg, A.; Reek, J. N. H.; Jagadeesh, R. V.; Beller, M. ChemSusChem 2019, 12, 3363. doi: 10.1002/cssc.v12.14
[46]	Tong, Z.; Peng, X.; Peng, L.; Deng, W.; Wang, Z.; Lu, H.; Yang, W.; Yin, S. F.; Kambe, N.; Qiu, R. J. Org. Chem. 2022, 87, 6064. doi: 10.1021/acs.joc.2c00325
[47]	Lee, M. T.; Goodstein, M. B.; Lalic, G. J. Am. Chem. Soc. 2019, 141, 17086. doi: 10.1021/jacs.9b09336
[48]	Lee, M. T.; Lalic, G., J. Am. Chem. Soc. 2021, 143, 1666.
[49]	Wu, S. W.; Liu, J. L.; Liu, F. Org. Lett. 2016, 18, 1. doi: 10.1021/acs.orglett.5b03069
[50]	Yu, J.; Zhou, Y.; Lin, Z.; Tong, R. Org. Lett. 2016, 18, 4734. doi: 10.1021/acs.orglett.6b02405
[51]	Das, J.; Vellakkaran, M.; Sk, M.; Banerjee, D. Org. Lett. 2019, 21, 7514. doi: 10.1021/acs.orglett.9b02793
[52]	Chen, K. Q.; Shen, J.; Wang, Z. X.; Chen, X. Y. Chem. Sci. 2021, 12, 6684. doi: 10.1039/D1SC01024G
[53]	Xia, S.; Cao, D.; Zeng, H.; He, L. N.; Li, C. J. JACS Au 2022, 2, 1929. doi: 10.1021/jacsau.2c00320
[54]	Liu, H.; Xu, M.; Cai, C.; Chen, J.; Gu, Y.; Xia, Y. Org. Lett. 2020, 22, 1193. doi: 10.1021/acs.orglett.0c00072
[55]	Wang, Y.; Qin, C.; Jia, X.; Leng, X.; Huang, Z. Angew. Chem., Int. Ed. 2017, 56, 1614. doi: 10.1002/anie.v56.6
[56]	Meng, Q. Y.; Schirmer, T. E.; Katou, K.; Konig, B. Angew. Chem. Int.,Ed. 2019, 58, 5723. doi: 10.1002/anie.v58.17
[57]	Kapat, A.; Sperger, T.; Guven, S.; Schoenebeck, F. Science 2019, 363, 391. doi: 10.1126/science.aav1610 pmid: 30679370
[58]	Yang, W.; Chernyshov, I. Y.; Weber, M.; Pidko, E. A.; Filonenko, G. A. ACS Catal. 2022, 12, 10818. doi: 10.1021/acscatal.2c02963
[59]	Esfandiarfard, K.; Mai, J.; Ott, S. J. Am. Chem. Soc. 2017, 139, 2940. doi: 10.1021/jacs.7b00428 pmid: 28186736
[60]	Das, U. K.; Chakraborty, S.; Diskin-Posner, Y.; Milstein, D. Angew. Chem., Int. Ed. 2018, 57, 13444. doi: 10.1002/anie.201807881
[61]	Lv, L.; Zhu, D.; Li, C. J. Nat. Commun. 2019, 10, 715. doi: 10.1038/s41467-019-08631-1
[62]	Li, W. H.; Li, C. Y.; Xiong, H. Y.; Liu, Y.; Huang, W. Y.; Ji, G. J.; Jiang, Z.; Tang, H. T.; Pan, Y. M.; Ding, Y. J. Angew. Chem. Int. Ed. 2019, 58, 2448. doi: 10.1002/anie.v58.8
[63]	Zhu, E.; Liu, X. X.; Wang, A. J.; Mao, T.; Zhao, L.; Zhang, X.; He, C. Y. Chem. Commun. 2019, 55, 12259. doi: 10.1039/C9CC06587C
[64]	Tao, L.; Guo, X.; Li, J.; Li, R.; Lin, Z.; Zhao, W. J. Am. Chem. Soc. 2020, 142, 18118. doi: 10.1021/jacs.0c07854
[65]	Nguyen, T. T.; Koh, M. J.; Shen, V.; Romiti, F.; Schrock, R.; Hoveyda, A. H. Science 2016, 352, 6285.
[66]	Szyling, J.; Walkowiak, J.; Sokolnicki, T.; Franczyk, A.; Stefano- wska, K.; Klarek, M. J. Catal. 2019, 376, 219. doi: 10.1016/j.jcat.2019.07.009
[67]	Swain, M.; Sadykhov, G.; Wang, R.; Kwon, O. Angew. Chem., Int. Ed. 2020, 59, 17565. doi: 10.1002/anie.v59.40
[68]	Karunananda, M. K.; Mankad, N. P. J. Am. Chem. Soc. 2015, 137, 14598. doi: 10.1021/jacs.5b10357 pmid: 26550848
[69]	Furukawa, S.; Komatsu, T. ACS Catal. 2016, 6, 2121. doi: 10.1021/acscatal.5b02953
[70]	Maazaoui, R.; Abderrahim, R.; Chemla, F.; Ferreira, F.; Perez-Luna, A.; Jackowski, O. Org. Lett. 2018, 20, 7544. doi: 10.1021/acs.orglett.8b03295
[71]	Pierce, B. M.; Simpson, B. F.; Ferguson, K. H.; Whittaker, R. E. Org. Biomol. Chem. 2018, 16, 6659. doi: 10.1039/c8ob01848k pmid: 30187050
[72]	Radkowski, K.; Sundararaju, B.; Furstner, A. Angew. Chem., Int. Ed. 2013, 52, 355. doi: 10.1002/anie.201205946 pmid: 22965553
[73]	Furstner, A. J. Am. Chem. Soc. 2019, 141, 11. doi: 10.1021/jacs.8b09782
[74]	Hu, M. Y.; He, P.; Qiao, T. Z.; Sun, W.; Li, W. T.; Lian, J.; Li, J. H.; Zhu, S. F. J. Am. Chem. Soc. 2020, 142, 16894. doi: 10.1021/jacs.0c09083
[75]	Magre, M.; Maity, B.; Falconnet, A.; Cavallo, L. Angew. Chem., Int. Ed. 2019, 58, 7025. doi: 10.1002/anie.201902188 pmid: 30977970
[76]	Zhang, J.; Wang, Z.; Chen, W.; Xiong, Y.; Cheong, W.-C.; Zheng, L.; Yan, W.; Gu, L.; Chen, C.; Peng, Q.; Hu, P.; Wang, D.; Li, Y. Chem 2020, 6, 725. doi: 10.1016/j.chempr.2019.12.021
[77]	Armstrong, M. K.; Goodstein, M. B.; Lalic, G. J. Am. Chem. Soc. 2018, 140, 10233 doi: 10.1021/jacs.8b05113 pmid: 30063341
[78]	Takahashi, K.; Ogiwara, Y.; Sakai, N. Chem. Asian. J. 2018, 13, 809. doi: 10.1002/asia.201701775
[79]	Hazra, A.; Chen, J.; Lalic, G. J. Am. Chem. Soc. 2019, 141, 12464. doi: 10.1021/jacs.9b04800
[80]	Hazra, A.; Kephart, J. A.; Velian, A.; Lalic, G. J. Am. Chem. Soc. 2021, 143, 7903. doi: 10.1021/jacs.1c03396
[81]	Molloy, J. J.; Metternich, J. B.; Daniliuc, C. G.; Watson, A. J. B.; Gilmour, R. Angew. Chem., Int. Ed. 2018, 57, 3168. doi: 10.1002/anie.201800286 pmid: 29393569
[82]	Zong, Y.; Tang, Y.; Tsui, G. C. Org. Lett. 2022, 24, 6380. doi: 10.1021/acs.orglett.2c02294
[83]	Mandal, S.; Verma, P. K.; Geetharani, K. Chem. Commun. 2018, 54, 13690. doi: 10.1039/C8CC08361D
[84]	Sun, Y.; Meng, K.; Zhang, J.; Jin, M.; Huang, N.; Zhong, G. Org. Lett. 2019, 21, 4868. doi: 10.1021/acs.orglett.9b01766
[85]	Yu, L.; Lv, L.; Qiu, Z.; Chen, Z.; Tan, Z.; Liang, Y. F.; Li, C. J. Angew. Chem., Int. Ed.. 2020, 59, 14009. doi: 10.1002/anie.v59.33
[86]	Liu, D. N.; Tian, S. K., Chem.-Eur. J. 2009, 15, 4538. doi: 10.1002/chem.v15:18
[87]	Cartwright, K. C.; Tunge, J. A. ACS Catal. 2018, 8, 1180.
[88]	Xiao, T.; Mei, M.; He, Y.; Zhou, L. Chem. Commun. 2018, 54, 8865. doi: 10.1039/C8CC04609C
[89]	Wu, G. J.; Von Wangelin, A. J. Chem. Sci. 2018, 9, 1795.
[90]	Li, K.; Zhang, X.; Chen, J.; Gao, Y.; Yang, C.; Zhang, K.; Zhou, Y.; Fan, B. Org. Lett. 2019, 21, 9914. doi: 10.1021/acs.orglett.9b03855
[91]	Gao, Y.; Wu, Z. Q.; Engle, K. M. Org. Lett. 2020, 22, 5235. doi: 10.1021/acs.orglett.0c01901
[92]	Ren, S.; Ye, B.; Li, S.; Pang, L.; Pan, Y.; Tang, H. Nano. Res. 2022, 15, 1500. doi: 10.1007/s12274-021-3694-3
[93]	Hu, L.; Gao, H.; Hu, Y.; Lv, X.; Wu, Y.-B.; Lu, G. Org. Chem. Front. 2022, 9, 1033. doi: 10.1039/D1QO01788H