炔丙醇类化合物参与的环化反应研究进展

doi:10.6023/cjoc202203037

摘要/Abstract

炔丙醇是一类具有醇羟基和碳碳叁键官能团的化合物. 由于该类化合物的特殊结构, 使其显示出独特的反应特性, 并可通过活化其醇羟基或叁键进而参与反应. 最为典型的是它们可与各类化合物发生多种形式的环化反应, 实现了种类繁多的环状化合物制备, 如环戊烯、吡咯、呋喃、环状碳酸酯、吡喃、吡啶和氮杂䓬类环状化合物. 综述了近年来炔丙醇类化合物参与的[3+2]、[2+3]、[3+3]、[4+2]、[2+4]、[4+1]、[3+4]和其它类型的环化反应.

关键词: 炔丙醇, 双官能团, 醇羟基, 碳碳叁键, 串联反应, 环化

Propargyl alcohols as a classical bifunctional group compounds possess alcohol hydroxyl group and carbon-carbon triple bond. Due to their special structure, they show unique reaction characteristics, and are employed in reactions via activating its alcoholic hydroxyl group or triple bond. The most typical reaction for propargyl alcohols is various cyclization reactions with different compounds to assemble a richer variety of cyclized compounds such as cyclopentene, pyrrole, furan, cyclic carbonate, pyran, pyridine and azepine cyclic compounds. The recent research progress in the cyclization reaction of propargyl alcohols with various compounds, including [3+2], [2+3], [3+3], [4+2], [2+4], [4+1], [3+4] and other types of cyclization reactions, is summarized.

Key words: propargyl alcohol, bifunctional group, alcohol hydroxyl, carbon-carbon triple bond, cascade reaction, cyclization

引用此文

赵晓正, 凌琴琴, 曹桂妍, 火星, 赵小龙, 苏瀛鹏. 炔丙醇类化合物参与的环化反应研究进展[J]. 有机化学, 2022, 42(9): 2605-2639.

Xiaozheng Zhao, Qinqin Ling, Guiyan Cao, Xing Huo, Xiaolong Zhao, Yingpeng Su. Research Progress in the Cyclization Reactions with Propargyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2605-2639.

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图/表 71

图式1. 炔丙醇参与的环化反应类型

Scheme 1. Cyclization reactions involving propargyl alcohol

图式2. 优先活化叁键启动的反应模式

Scheme 2. Pre-activation of the triple bond induced reaction mode

图式3. 优先活化羟基启动的反应模式

Scheme 3. Pre-activation of the hydroxyl induced reaction mode

图式4. BF3•Et2O催化的炔丙醇与二硫缩醛烯基酮的串联环化反应

Scheme 4. BF3•Et2O-catalyzed cascade cyclization reaction of propargyl alcohol and ketene dithioacetal

图式5. 银催化的炔丙醇与吲哚的串联环化反应

Scheme 5. Silver-catalyzed cascade cyclization reaction of propargyl alcohol and indole

图式6. 金催化的炔丙醇与叠氮化物的串联环化反应

Scheme 6. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and azide

图式7. 手性磷酸催化的炔丙醇与吲哚的不对称串联环化反应

Scheme 7. Chiral phosphoric acid-catalyzed asymmetric cascade cyclization reaction of propargyl alcohol and indole

图式8. t-BuOK催化的炔丙醇与肼的串联环化反应

Scheme 8. t-BuOK-catalyzed cascade cyclization reaction of propargyl alcohol and hydrazine

图式9. DABCO催化的炔丙醇与2-三氟甲基炔酸甲酯的串联环化反应

Scheme 9. DABCO-catalyzed cascade cyclization reaction of propargyl alcohol and methyl 2-perfluoroalkynoate

图式10. 金催化的炔丙醇与炔烃的串联环化反应

Scheme 10. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and alkyne

图式11. Et3N参与的炔丙醇与芳基羧酸的串联环化反应

Scheme 11. Et3N-mediated cascade cyclization reaction of propargyl alcohol and aryl carboxylic acid

图式12. t-BuOI促进的炔丙醇与CO2的串联环化反应

Scheme 12. t-BuOI-promoted cascade cyclization reaction of propargyl alcohol and CO2

图式13. 银催化的炔丙醇与CO2的串联环化反应

Scheme 13. Silver-catalyzed cascade cyclization reaction of propargyl alcohol and CO2

图式14. 电催化的炔丙醇与CO2的串联环化反应

Scheme 14. Electro-catalyzed cascade cyclization reaction of propargyl alcohol and CO2

图式15. MTBD催化的炔丙醇与CO2的串联环化反应

Scheme 15. MTBD-catalyzed cascade cyclization reaction of propargyl alcohol and CO2

图式16. 银催化的炔丙醇与CO2的串联环化反应

Scheme 16. Silver-catalyzed cascade cyclization reaction of propargyl alcohol and CO2

图式17. Ag(I)-DavePhos催化炔丙醇与CO2的羧化环化反应能量图

Scheme 17. Energy diagram of the carboxylation cyclization of propargyl alcohol with CO2 catalyzed by Ag(I)-DavePhos

图式18. NaOtP促进的炔丙醇与CO2的串联环化反应

Scheme 18. NaOtP-promoted cascade cyclization reaction of propargyl alcohol and CO2

图式19. 钙催化的炔丙醇与芳基烯烃的串联环化反应

Scheme 19. Calcium-catalyzed cascade cyclization reaction of propargyl alcohol and aryl olefin

图式20. 铁催化的炔丙醇与酚的串联环化反应

Scheme 20. Iron-catalyzed cascade cyclization reaction of propargyl alcohol and phenol

图式21. 钙催化的炔丙醇与2-萘酚的串联环化反应

Scheme 21. Calcium-catalyzed cascade cyclization reaction of propargyl alcohol and 2-naphthol

图式22. Bu4NPF6介导的炔丙醇与萘酚的串联环化反应

Scheme 22. Bu4NPF6-mediated cascade cyclization reaction of propargyl alcohol and naphthol

图式23. 锌催化的炔丙醇与氨基咔唑的串联环化反应

Scheme 23. Zinc-catalyzed cascade cyclization reaction of propargyl alcohol and aminocarbazole

图式24. 钌催化下炔丙醇与N-吡啶苯胺的串联环化反应

Scheme 24. Ruthenium-catalyzed cascade cyclization reaction of propargyl alcohol and N-pyridineaniline

图式25. 铝催化下炔丙醇与氨基嘧啶的串联环化反应

Scheme 25. Aluminium-catalyzed cascade cyclization reaction of propargyl alcohol and aminopyrimidine

图式26. 铑催化的炔丙醇与N-亚硝基苯胺的串联环化反应

Scheme 26. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and N-nitrosoaniline

图式27. 镱催化的炔丙醇与2-吲哚甲醇或苯甲醇的串联环化反应

Scheme 27. Ytterbium-catalyzed cascade cyclization reaction of propargyl alcohol and 2-indolecarbinol or benzyl alcohol

图式28. 钙催化的炔丙醇与环烯醇的串联环化反应

Scheme 28. Calcium-catalyzed cascade cyclization reaction of propargyl alcohol and cycloenol

图式29. TFA介导的炔丙醇与1,3-二酮的串联环化反应

Scheme 29. TFA-mediated cascade cyclization reaction of propargyl alcohol and 1,3-dione

图式30. BF3•Et2O促进的炔丙醇与3-(1,3-二硫噻吩)丙烯酰胺/羧酸的串联环化反应

Scheme 30. BF3•Et2O-promoted cascade cyclization reaction of propargyl alcohol and 3-(1,3-dithiothiophene) acrylamide or carboxylic acid

图式31. 铑催化的炔丙醇与重氮萘醌的串联环化反应

Scheme 31. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and diazonaphthoquinone

图式32. BF3•Et2O催化的炔丙醇与烯胺酮的串联环化反应

Scheme 32. BF3•Et2O-catalyzed cascade cyclization reaction of propargyl alcohol and enaminone

图式33. BF3•Et2O促进的炔丙醇与伯胺和2-丁炔二羧酸甲酯的串联环化反应

Scheme 33. BF3•Et2O-promoted cascade cyclization reaction of propargyl alcohol and primary amine and methyl 2-butynedicarboxylate

图式34. 钯/铜催化的炔丙醇与1-氨基-2-溴吡咯的串联环化反应

Scheme 34. Palladium/copper-catalyzed cascade cyclization reaction of propargyl alcohol and 1-amino-2-bromopyrrole

图式35. 金催化的炔丙醇与氮丙啶的串联环化反应

Scheme 35. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and aziridine

图式36. 铁催化的炔丙醇与芳胺的串联环化反应

Scheme 36. Iron-catalyzed cascade cyclization reaction of propargyl alcohol and aromatic amine

图式37. 碘介导的炔丙醇与芳基叠氮化物的串联环化反应

Scheme 37. Iodine-mediated cascade cyclization reaction of propargyl alcohol and aryl azides

图式38. 银催化的炔丙醇与3-亚甲基异吲哚-1-酮的串联环化反应

Scheme 38. Silver-catalyzed cascade cyclization reaction of propargyl alcohol and 3-methyleneisoindol-1-one

图式39. 金催化的炔丙醇与亚胺的串联环化反应

Scheme 39. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and imine

图式40. 联合催化下炔丙醇与2-羟基硝基苯乙烯的串联环化反应

Scheme 40. Dual-catalyzed cascade cyclization reaction of propargyl alcohol and 2-hydroxynitrostyrene.

图式41. 钌催化下炔丙醇与苯甲亚胺酯的串联环化反应

Scheme 41. Ruthenium-catalyzed cascade cyclization reaction of propargyl alcohol and benzyl imide

图式42. 在二氯甲烷溶液中获得的吉布斯自由能曲线

Scheme 42. Gibb's free energy profile in DCM solvent

图式43. 钌和碱催化下炔丙醇与N-对甲苯磺酰基苯甲酰胺的分步环化反应

Scheme 43. Ruthenium and base-catalyzed two-step cyclization reaction of propargyl alcohol and N-p-toluenesulfonylbenzamide

图式44. 铑催化的炔丙醇与肟的串联环化反应

Scheme 44. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and oxime

图式45. 铑催化的炔丙醇与3-芳基异噁唑酮的串联环化反应

Scheme 45. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and 3-arylisoxazolone

图式46. 铑催化的炔丙醇与苯甲酸的串联环化反应

Scheme 46. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and benzoic acid

图式47. 铜催化的炔丙醇与腈的串联环化反应

Scheme 47. Copper-catalyzed cascade cyclization reaction of propargyl alcohol and nitrile

图式48. 金催化的炔丙醇与吡啶N-氧化物的串联环化反应

Scheme 48. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and pyridine N-oxide

图式49. 两种可能的转化反应和活化势垒的计算过渡态

Scheme 49. Calculated transition states for the two conceivable shift reactions and the activation barriers

图式50. 金催化的炔丙醇与水的串联环化反应

Scheme 50. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and water

图式51. 金催化的炔丙醇与α-重氮酯的串联环化反应

Scheme 51. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and α-diazoester

图式52. 钯催化的炔丙醇与α-重氮酯的串联环化反应

Scheme 52. Palladium-catalyzed cascade cyclization reaction of propargyl alcohol and α-diazoester

图式53. 钯催化的炔丙醇与TFBen的串联环化反应

Scheme 53. Palladium-catalyzed cascade cyclization reaction of propargyl alcohol and TFBen

图式54. 钯催化炔丙醇与芳基三氟甲磺酸酯的串联环化反应

Scheme 54. Palladium-catalyzed cascade cyclization reaction of propargyl alcohol and aryl triflate

图式55. 金催化的炔丙醇与羟胺的串联环化反应

Scheme 55. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and hydroxylamine

图式56. 金催化的炔丙醇与邻苯二胺的串联环化反应

Scheme 56. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and o-phenylenediamine

图式57. 钇催化的炔丙醇与2-叠氮甲基-1H-吲哚的串联环化反应

Scheme 57. Yttrium-catalyzed cascade cyclization reaction of propargyl alcohol and 2-azidomethyl-1H-indole

图式58. 铜催化炔丙醇与吲哚-2-羧酸/酰胺的串联环化反应

Scheme 58. Copper-catalyzed cascade cyclization reaction of propargyl alcohol and indole-2-carboxylic acid or amide

图式59. p-TSA催化炔丙醇与吲哚-3-酰胺的串联环化反应

Scheme 59. p-TSA-catalyzed cascade cyclization reaction of propargyl alcohol and indole-3-amide

图式60. BF3•Et2O促进的炔丙醇与仲胺和2-丁炔二羧酸酯的串联环化反应

Scheme 60. BF3•Et2O-promoted cascade cyclization reaction of propargyl alcohol and secondary amine and 2-butynedicarboxylates

图式61. 2,2',2''-三联吡啶催化的炔丙醇与伯胺和CO2的串联环化反应

Scheme 61. 2,2',2''-Terpyridine-catalyzed cascade cyclization reaction of propargyl alcohol and primary amines and CO2

图式62. 金/铜催化炔丙醇与吡啶基高炔丙醇的串联环化反应

Scheme 62. Gold/copper-catalyzed cascade cyclization reaction of propargyl alcohol and pyridyl homopropargyl alcohol

图式63. 钌催化下炔丙醇与芳基偶氮甲亚胺的串联环化反应

Scheme 63. Ruthenium-catalyzed cascade cyclization reaction of propargyl alcohol and arylazocarbimide

图式64. 金催化的炔丙醇的分子内环化反应

Scheme 64. Gold-catalyzed intro-molecular cyclization of propargyl alcohol

图式65. 金催化的炔丙醇与1,3,5-三甲苯的串联环化反应

Scheme 65. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and 1,3,5-trimethylbenzene

图式66. 金催化的炔丙醇的串联环化反应

Scheme 66. Gold-catalyzed cascade cyclization reaction of propargyl alcohol

图式67. 钯催化的炔丙醇与胺的环化-胺化串联反应

Scheme 67. Palladium-catalyzed cascade cyclization-amination of propargyl alcohol and amine

图式68. MsOH促进的炔丙醇的串联环化反应

Scheme 68. MsOH-promoted cascade cyclization reaction of propargyl alcohol

图式69. 银催化的炔丙醇的串联环化反应

Scheme 69. Silver-catalyzed cascade cyclization reaction of propargyl alcohol

图式70. p-TsOH催化或碘参与的炔丙醇的串联环化反应

Scheme 70. p-TsOH-catalyzed or iodine-mediated cascade cyclization reaction of propargyl alcohol

图式71. 铜催化的炔丙醇与二芳基膦氧化物的串联环化反应

Scheme 71. Copper-catalyzed cascade cyclization reaction of propargyl alcohol and diarylphosphine oxide

参考文献 76

[1]	(a) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208. doi: 10.1039/b816696j pmid: 19847352
	(b) Xu, W.; Zhao, S.; Luo, X.; Song, J.; Liu, J.; Bi, X.; Liao, P. Chin. J. Org. Chem. 2015, 35, 2095. (in Chinese) doi: 10.6023/cjoc201505025 pmid: 19847352
	(徐文帅, 赵寿经, 骆晓沛, 宋金娜, 刘建全, 毕锡合, 廖沛球, 有机化学, 2015, 35, 2095.) doi: 10.6023/cjoc201505025 pmid: 19847352
[2]	(a) Garayalde, D.; Nevado, C. ACS Catal. 2012, 2, 1462. doi: 10.1021/cs300043w
	(b) Kazem Shiroodi, R.; Gevorgyan, V. Chem. Soc. Rev. 2013, 42, 4991. doi: 10.1039/c3cs35514d
	(c) Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448. doi: 10.1039/C1CS15279C
	(d) Zhang, X.; Lü, C.; Li, P.; Fu, B.; Yao, W. Chin. J. Org. Chem. 2016, 36, 1287. (in Chinese) doi: 10.6023/cjoc201512003
	(张小祥, 吕昌, 李萍, 付博, 姚薇薇, 有机化学, 2016, 36, 1287.)
[3]	(a) Bi, X.; Zhang, L.; Fang, G.; Kumar, R. Synthesis 2015, 47, 2317. doi: 10.1055/s-0034-1378852
	(b) Chan, P.; Ayers, B. Synlett 2015, 26, 1305. doi: 10.1055/s-0034-1380402
	(c) Weibel, J.-M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149. doi: 10.1021/cr078365q
	(d) Zhu, Y.; Sun, L.; Lu, P.; Wang, Y. ACS Catal. 2014, 4, 1911. doi: 10.1021/cs400922y
[4]	Qian, H.; Huang, D.; Bi, Y.; Yan, G. Adv. Synth. Catal. 2019, 361, 3240. doi: 10.1002/adsc.201801719
[5]	Liu, X.-Y.; Liu, Y.-L.; Chen, L. Adv. Synth. Catal. 2020, 362, 5170 doi: 10.1002/adsc.202000930
[6]	Fang, Z.; Liu, J.; Liu, Q.; Bi, X. Angew. Chem., nt. Ed. 2014, 53, 7209.
[7]	Hao, L.; Pan, Y.; Wang, T.; Lin, M.; Chen, L.; Zhan, Z.-P. Adv. Synth. Catal. 2010, 352, 3215 doi: 10.1002/adsc.201000525
[8]	Li, N.; Wang, T.-Y.; Gong, L.-Z.; Zhang, L. Chem.-Eur. J. 2015, 21, 3585. doi: 10.1002/chem.201406456
[9]	Bai, J.-F.; Zhao, L.; Wang, F.; Yan, F.; Kano, T.; Maruoka, K.; Li, Y. Org. Lett. 2020, 22, 5439. doi: 10.1021/acs.orglett.0c01812
[10]	Wang, X.; Pan, Y.-M.; Huang, X.-C.; Mao, Z.-Y.; Wang, H.-S. Org. Biomol. Chem. 2014, 12, 2028. doi: 10.1039/c3ob42432d pmid: 24519368
[11]	Chong, Q.; Xin, X.; Wang, C.; Wu, F.; Wang, H.; Shi, J.-C.; Wan, B. J. Org. Chem. 2014, 79, 2105. doi: 10.1021/jo4028424
[12]	Hosseyni, S.; Su, Y.; Shi, X. Org. Lett. 2015, 17, 6010. doi: 10.1021/acs.orglett.5b02980
[13]	Trofimov, B. A.; Shemyakina, O. A.; Mal'kina, A. G.; Ushakov, I. A.; Kazheva, O. N.; Alexandrov, G. G.; Dyachenko, O. A. Org. Lett. 2010, 12, 3200. doi: 10.1021/ol1011532 pmid: 20536165
[14]	Minakata, S.; Sasaki, I.; Ide, T. Angew. Chem., nt. Ed. 2010, 49, 1309.
[15]	Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T. J. Am. Chem. Soc. 2010, 132, 4072. doi: 10.1021/ja1007118
[16]	Yuan, G.-Q.; Zhu, G.-J.; Chang, X.-Y.; Qi, C.-R.; Jiang, H.-F. Tetrahedron 2010, 66, 9981. doi: 10.1016/j.tet.2010.10.039
[17]	Ca, N. D.; Gabriele, B.; Ruffolo, G.; Veltri, L.; Zanetta, T.; Costa, M. Adv. Synth. Catal. 2011, 353, 133. doi: 10.1002/adsc.201000607
[18]	Song, Q.-W.; Yu, B.; Li, X.-D.; Ma, R.; Diao, Z.-F.; Li, R.-G.; Li, W.; He, L.-N. Green Chem. 2014, 16, 1633. doi: 10.1039/c3gc42406e
[19]	Dabral, S.; Bayarmagnai, B.; Hermsen, M.; Schießl, J.; Mormul, V.; Hashmi, A. S. K.; Schaub, T. Org. Lett. 2019, 21, 1422. doi: 10.1021/acs.orglett.9b00156
[20]	Yan, S.; Zhou, R.; Han, F.; Feng, M.; Miao, C.; Zhang, S.; Ai, S. Catal. Sci. Technol. 2020, 10, 736. doi: 10.1039/C9CY02311A
[21]	Yaragorla, S.; Pareek, A.; Dada, R. Adv. Synth. Catal. 2017, 359, 3068. doi: 10.1002/adsc.201700569
[22]	Yuan, F.-Q.; Han, F.-S. Adv. Synth. Catal. 2013, 355, 537.
[23]	Yaragorla, S.; Dada, R.; Singh, G.; Pareek, A.; Rana, M.; Sharma, A. K. ChemistrySelect 2016, 1, 6902. doi: 10.1002/slct.201601349
[24]	Pareek, A.; Dada, R.; Rana, M.; Sharma, A. K.; Yaragorla, S. RSC Adv. 2016, 6, 89732. doi: 10.1039/C6RA17411F
[25]	Yaragorla, S.; Dada, R.; Pareek, A.; Singh, G. RSC Adv. 2016, 6, 28865. doi: 10.1039/C6RA03042D
[26]	Viji, M.; Nagarajan, R. RSC Adv. 2012, 2, 10544. doi: 10.1039/c2ra21735j
[27]	Kumar, M. P.; Liu, R.-S. J. Org. Chem. 2006, 71, 4951. doi: 10.1021/jo0606711
[28]	Bai, L.; Wang, Y.; Wang, S.; Kong, D.; Fu, Y.; Peng, D.; Wen, L.; Chen, X. Chin. J. Org. Chem. 2018, 38, 3242. (in Chinese) doi: 10.6023/cjoc201806039
	(白丽丽, 王颖, 王烁今, 孔杜林, 付艳, 彭德乾, 文丽君, 陈训, 有机化学, 2018, 38, 3242.) doi: 10.6023/cjoc201806039
[29]	Ponra, S.; Gohain, M.; Donka, R.; van Tonder, J. H.; Bezuidenhoudt, B. C. B. Tetrahedron Lett. 2018, 59, 2909. doi: 10.1016/j.tetlet.2018.06.039
[30]	Song, X.; Gao, C.; Li, B.; Zhang, X.; Fan, X. J. Org. Chem. 2018, 83, 8509. doi: 10.1021/acs.joc.8b01098 pmid: 29898599
[31]	Wang, S.; Chai, Z.; Wei, Y.; Zhu, X.; Zhou, S.; Wang, S. Org. Lett. 2014, 16, 3592. doi: 10.1021/ol501605h
[32]	Zeng, H.; Ju, J.; Hua, R. Tetrahedron Lett. 2011, 52, 3926. doi: 10.1016/j.tetlet.2011.05.093
[33]	Yaragorla, S.; Pareek, A.; Dada, R. Tetrahedron Lett. 2017, 58, 4642. doi: 10.1016/j.tetlet.2017.10.077
[34]	Han, Y.-P.; Li, X.-S.; Zhu, X.-Y.; Sun, Z.; Li, M.; Wang, Y.-Z.; Liang, Y.-M. Adv. Synth. Catal. 2018, 360, 870. doi: 10.1002/adsc.201701296
[35]	Liu, Y.; Barry, B.-D.; Yu, H.; Liu, J.; Liao, P.; Bi, X. Org. Lett. 2013, 15, 2608. doi: 10.1021/ol4007772
[36]	Kitamura, M.; Nishimura, T.; Otsuka, K.; Shimooka, H.; Okauchi, T. Tetrahedron Lett. 2020, 61, 151853. doi: 10.1016/j.tetlet.2020.151853
[37]	Su, J.; Ju, J.; Hua, R. Curr. Org. Synth. 2012, 9, 273. doi: 10.2174/157017912799829030
[38]	Shao, Y.; Zhu, K.; Qin, Z.; Li, E.; Li, Y. J. Org. Chem. 2013, 78, 5731. doi: 10.1021/jo4005553
[39]	Yin, G.; Zhu, Y.; Wang, N.; Lu, P.; Wang, Y. Tetrahedron 2013, 69, 8353. doi: 10.1016/j.tet.2013.07.076
[40]	Wang, M.; Tan, C.; He, Q.; Xie, Y.; Yang, C. Org. Biomol. Chem. 2013, 11, 2574. doi: 10.1039/c3ob40157j
[41]	Zhang, S.; Shan, C.; Zhang, S.; Yuan, L.; Wang, J.; Tung, C.-H.; Xing, L.-B.; Xu, Z. Org. Biomol. Chem. 2016, 14, 10973. doi: 10.1039/C6OB02284G
[42]	Shao, M.; Wu, Y.; Feng, Z.; Gu, X.; Wang, S. Org. Biomol. Chem. 2016, 14, 2515. doi: 10.1039/c5ob02658j pmid: 26820189
[43]	Wu, Y.; Shao, M.; Feng, Z.; Gu, X.; Hong, Y.; Cui, Q.; Ren, L.; Wang, S. Asian J. Org. Chem. 2017, 6, 76. doi: 10.1002/ajoc.201600503
[44]	Li, X.-S.; Han, Y.-P.; Xu, D.-T.; Li, M.; Wei, W.-X.; Liang, Y.-M. J. Org. Chem. 2020, 85, 2626. doi: 10.1021/acs.joc.9b02533
[45]	Wang, L.; Xie, X.; Liu, Y. Angew. Chem., nt. Ed. 2013, 52, 13302.
[46]	Rueping, M.; Dufour, J.; Maji, M. S. Chem. Commun. 2012, 48, 3406. doi: 10.1039/c2cc00129b
[47]	Anukumar, A.; Tamizmani, M.; Jeganmohan, M. J. Org. Chem. 2018, 83, 8567. doi: 10.1021/acs.joc.8b01123 pmid: 29799194
[48]	Kumar, S.; Nair, A. M.; Volla, C. M. R. Chem. Commun. 2021, 57, 6280. doi: 10.1039/D1CC01768C
[49]	Li, Y.; Fang, F.; Zhou, J.; Li, J.; Wang, R.; Liu, H.; Zhou, Y. Adv. Synth. Catal. 2021, 363, 3305. doi: 10.1002/adsc.202100239
[50]	Wang, T.-T.; Jin, H.-S.; Cao, M.-M.; Wang, R.-B.; Zhao, L.-M. Org. Lett. 2021, 23, 5952. doi: 10.1021/acs.orglett.1c02049
[51]	Luo, F.; He, S.; Gou, Q.; Chen, J.; Zhang, M. Tetrahedron Lett. 2021, 64, 152724. doi: 10.1016/j.tetlet.2020.152724
[52]	Qi, C.; Jiang, H.; Huang, L.; Yuan, G.; Ren, Y. Org. Lett. 2011, 13, 5520. doi: 10.1021/ol202241r
[53]	Wang, T.; Shi, S.; Hansmann, M. M.; Rettenmeier, E.; Rudolph, M.; Hashmi, A. S. K. Angew. Chem., nt. Ed. 2014, 53, 3715
[54]	Zhang, B.; Wang, T.; Zhang, Z. J. Org. Chem. 2017, 82, 11644 doi: 10.1021/acs.joc.7b01997 pmid: 28967246
[55]	Wang, J.; Yao, X.; Wang, T.; Han, J.; Zhang, J.; Zhang, X.; Wang, P.; Zhang, Z. Org. Lett. 2015, 17, 5124. doi: 10.1021/acs.orglett.5b02663
[56]	Shi, T.; Guo, X.; Teng, S.; Hu, W. Chem. Commun. 2015, 51, 15204. doi: 10.1039/C5CC05000F
[57]	Le, Z.; Ying, J.; Wu, X.-F. Org. Chem. Front. 2019, 6, 3158. doi: 10.1039/C9QO00779B
[58]	Ying, J.; Le, Z.; Wu, X.-F. Org. Chem. Front. 2020, 7, 2757. doi: 10.1039/D0QO00874E
[59]	Hsu, Y.-C.; Hsieh, S.-A.; Li, P.-H.; Liu, R.-S. Chem. Commun. 2018, 54, 2114. doi: 10.1039/C8CC00330K
[60]	Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Iazzetti, A. Org. Lett. 2016, 18, 3511. doi: 10.1021/acs.orglett.6b01720
[61]	Han, Y.-P.; Song, X.-R.; Qiu, Y.-F.; Zhang, H.-R.; Li, L.-H.; Jin, D.-P.; Sun, X.-Q.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 940. doi: 10.1021/acs.orglett.5b03657
[62]	Selvaraj, K.; Debnath, S.; Swamy, K. C. K. Org. Lett. 2019, 21, 5447. doi: 10.1021/acs.orglett.9b01686 pmid: 31246037
[63]	Yin, G.; Zhu, Y.; Lu, P.; Wang, Y. J. Org. Chem. 2011, 76, 8922. doi: 10.1021/jo2016407
[64]	Xu, J.; Zhao, J.; Jia, Z.; Zhang, J. Synth. Commun. 2011, 41, 858. doi: 10.1080/00397911003707014
[65]	Liu, H.; Hua, R. Tetrahedron 2016, 72, 1200. doi: 10.1016/j.tet.2016.01.015
[66]	Hussain, M. K.; Ansari, M. I.; Kant, R.; Hajela, K. Org. Lett. 2014, 16, 560. doi: 10.1021/ol403420z pmid: 24350729
[67]	Li, X.-S.; Xu, D.-T.; Niu, Z.-J.; Li, M.; Shi, W.-Y.; Wang, C.-T.; Wei, W.-X.; Liang, Y.-M. Org. Lett. 2021, 23, 832. doi: 10.1021/acs.orglett.0c04070
[68]	Zhang, L.; Zhao, J.; Jiang, Y.; Zhang, X.; Fan, X. Org. Chem. Front. 2021, 8, 3734. doi: 10.1039/D1QO00025J
[69]	Ye, L.; He, W.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 8550. doi: 10.1021/ja1033952
[70]	Morita, N.; Miyamoto, M.; Yoda, A.; Yamamoto, M.; Ban, S.; Hashimoto, Y.; Tamura, O. Tetrahedron Lett. 2016, 57, 4460. doi: 10.1016/j.tetlet.2016.08.045
[71]	Egi, M.; Azechi, K.; Saneto, M.; Shimizu, K.; Akai, S. J. Org. Chem. 2010, 75, 2123 doi: 10.1021/jo100048j
[72]	Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Molinaro, C.; Verdiglione, R. J. Org. Chem. 2014, 79, 401 doi: 10.1021/jo401456x
[73]	Tharra, P.; Baire, B. J. Org. Chem. 2015, 80, 8314 doi: 10.1021/acs.joc.5b01420
[74]	Egi, M.; Ota, Y.; Nishimura, Y.; Shimizu, K.; Azechi, K.; Akai, S. Org. Lett. 2013, 15, 4150 doi: 10.1021/ol401824v
[75]	Qiu, Y.-F.; Ye, Y.-Y.; Song, X.-R.; Zhu, X.-Y.; Yang, F.; Song, B.; Wang, J.; Hua, H.-L.; He, Y.-T.; Han, Y.-P.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2015, 21, 3480. doi: 10.1002/chem.201406100
[76]	Li, R.; Chen, X.; Song, X.-R.; Ding, H.; Wang, P.; Xiao, Q.; Liang, Y.-M. Adv. Synth. Catal. 2017, 359, 3962. doi: 10.1002/adsc.201700985