C—N轴手性化合物的不对称催化合成研究进展

doi:10.6023/cjoc202308012

摘要/Abstract

C—N轴手性化合物在天然产物、手性药物以及手性配体等诸多领域有着广泛应用, 通过不对称催化高效构建 C—N轴手性受到越来越广泛的关注. 此文旨在综述近年国内外在C—N轴手性化合物不对称催化合成方面取得的研究进展, 主要从前手性分子的去对称化或外消旋体的动力学拆分、C—N轴的阻旋选择性官能团化以及阻旋选择性C—N偶联等三方面进行讨论. 重点关注不对称催化体系的发展以及控制对映选择性的关键因素, 并对该领域存在的问题和未来发展方向进行讨论.

关键词: C—N轴手性化合物, 不对称催化, 阻旋选择性, 去对称化

Enantioenriched C—N axial chiral compounds are ubiquitous in many important field, such as natural products, chiral drugs and chiral ligands. Therefore, efficient construction of C—N axis chirality through asymmetric catalytic synthesis has attracted more and more attention and research interest. In this review, the recent progress in asymmetric synthesis of C—N axis chiral compounds has been discussed, mainly from three aspects: desymmetrization of prochiral molecules or kinetic resolution of racemates, atroposelective functionalization of C—N axis, and atroposelective C—N coupling reaction. The topic focuses on the evolution of asymmetric catalytic system and the key factors of chiral control. The existing problems and future development direction of this field are also discussed. This paper is a timely and systematic review and will stimulate more extensive research interest.

Key words: C—N axis chiral compounds, desymmetrization, asymmetric catalysis, atroposelective

引用此文

陈宛婷, 钟雄威, 邢佳乐, 吴昌书, 高杨. C—N轴手性化合物的不对称催化合成研究进展[J]. 有机化学, 2024, 44(2): 349-377.

Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.

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图/表 64

图式1. C—N轴手性化合物的重要性和不对称催化合成策略

Scheme 1. Enantioenriched C—N axial chiral compounds and asymmetric catalytic strategies

图式2. N-芳基马来酰亚胺的去对称化

Scheme 2. Desymmetrization of N-aryl maleimide

图式3. 铑催化N-芳基马来酰亚胺的不对称1,4-加成反应

Scheme 3. Rh-catalyzed asymmetric 1,4-addition of N-aryl maleimide

图式4. 铑催化N-芳基马来酰亚胺的不对称氢芳基化反应

Scheme 4. Rh-catalyzed asymmetric hydroarylation of N-aryl maleimide

图式5. 铑催化降冰片烯衍生物的不对称碳胺化反应

Scheme 5. Rh-catalyzed asymmetric carboamination of norbornene derivative

图式6. 镍催化降冰片烯衍生物的不对称氢腈化反应

Scheme 6. Ni-catalyzed asymmetric hydronitridation of norbornene derivative

图式7. 钯催化N-芳基马来酰亚胺的不对称硅氢化反应

Scheme 7. Pd-catalyzed asymmetric hydrosilylation of N-aryl maleimide

图式8. 银催化1,3-偶极环加成去对称化反应

Scheme 8. Ag-catalyzed asymmetric 1,3-dipolar cycloaddition

图式9. N-芳基马来酰亚胺的加成/环加成

Scheme 9. Addition/cycloaddition of N-aryl maleimide

图式10. N-芳基马来酰亚胺Michal加成去对称化

Scheme 10. Desymmetrization of N-aryl maleimide via Michal addition

图式11. 钪催化N-芳基马来酰亚胺的Michal加成去对称化

Scheme 11. Sc-catalyzed desymmetrization of N-aryl maleimide via Michal addition

图式12. NHC催化N-芳基马来酰亚胺的去对称化

Scheme 12. NHC-catalyzed desymmetrization of N-aryl maleimide

图式13. NHC催化N-芳基脲唑的对映选择性去对称

Scheme 13. NHC-catalyzed desymmetrization of N-aryl urease

图式14. 4-芳基-1,2,4-三唑-3,5-二酮的去对称化

Scheme 14. Desymmetrization of 4-aryl-1,2,4-triazole-3,5-dione

图式15. 1,2,4-三唑-3,5-二酮的ene反应去对称化

Scheme 15. Desymmetrization of 1,2,4-triazole-3,5-dione via ene reaction

图式16. 轴手性N-芳基吡咯的合成

Scheme 16. Synthesis of of axial chiral N-arylpyrroles

图式17. 钯催化脱溴氢化去对称化

Scheme 17. Pd-catalyzed debromination hydrogenation desymmetrization

图式18. 手性多肽催化阻旋选择性亲电溴代

Scheme 18. Chiral peptide-catalyzed atroposelective bromination

图式19. 手性磷酸催化阻旋选择性亲电溴代

Scheme 19. Chiral phosphoric acid-catalyzed atroposelective electrophilic bromination

图式20. 阻旋选择性Pictet-Spengler反应

Scheme 20. Atroposelective Pictet-Spengler reaction

图式21. 手性NHC催化动力学拆分

Scheme 21. NHC-catalyzed kinetic resolution of anilides

图式22. 不对称N-烯丙基化构建轴手性酰胺/磺酰胺

Scheme 22. Synthesis of atropisomeric anilides through enantioselective N-allylation

图式23. 双奎宁有机碱催化不对称N-烯丙基化

Scheme 23. Asymmetric N-allylation catalyzed by double quinine organic bases

图式24. 羟基奎宁催化膦酰胺的N-烯丙基化反应

Scheme 24. N-Allylation reaction of phosphamides catalyzed by hydroxyquinine

图式25. 钯催化酰胺的不对称N-芳基化/酰基化

Scheme 25. Pd-catalyzed asymmetric N-arylation/acylation of amides

图式26. 手性硫脲催化的阻旋选择性N-酰化反应

Scheme 26. Chiral thiourea catalyzed atroposelective N-acylation

图式27. 手性相转移催化剂催化的不对称N-烷基化

Scheme 27. Chiral phase transfer catalyzed asymmetric N-alkylation

图式28. 钯催化的不对称碳氢键官能团化

Scheme 28. Pd-catalyzed asymmetric C—H functionalization

图式29. 手性辅基导向的不对称炔基化

Scheme 29. Chiral auxiliary group-directed asymmetric C—H alkylation

图式30. 手性辅基导向的不对称碳氢键烯基化

Scheme 30. Chiral auxiliary group-directed asymmetric C—H olefination

图式31. 钯催化氨基导向的不对称碳氢键烯基化

Scheme 31. Pd-catalyzed amine-directed asymmetric C—H olefination

图式32. 铑催化不对碳酰胺化构建轴手性和中心手性

Scheme 32. Rh-catalyzed construction of axial chirality and central chirality via asymmetric carboamidation

图式33. 钯催化阻旋选择性C—N偶联反应

Scheme 33. Pd-catalyzed atroposelective C—N coupling

图式34. 铜催化阻旋选择性C—N偶联化反应

Scheme 34. Cu-catalyzed atroposelective C—N coupling

图式35. 钯催化阻旋选择性Catellani反应/插羰反应

Scheme 35. Pd-catalyzed atroposelective Catellani reaction/carbonyl insertion reaction

图式36. 炔烃的阻旋选择性氮环化反应

Scheme 36. Atroposelective aza-cycloaddition reaction of alkynes

图式37. 手性胍催化炔烃异构化/Michael加成环化反应

Scheme 37. Chiral guanidine-catalyzed tandem isomerization/ Michael reactions of alkynes

图式38. 光催化合成N—C轴手性杂环化合物

Scheme 38. Photocatalytic synthesis of N—C axial chiral heterocycles

图式39. 手性磷酸催化阻旋选择性分子内酰胺化反应

Scheme 39. Chiral phosphoric acid catalyzed atroposelective intramolecular acylation reaction

图式40. 铑催化不对称碳氢键活化/插炔环化反应

Scheme 40. Rh-catalyzed asymmetric C—H activation/acetylene insertion annulation

图式41. 铑催化碳氢键活化和阻旋选择性环化反应

Scheme 41. Rh-catalyzed C—H activation and atroposelective annulation

图式42. Co/Salox催化的不对称碳氢键活化/环化反应

Scheme 42. Co/Salox-catalyzed asymmetric C—H activation/annulation

图式43. 手性磷酸催化阻旋选择性Paal-Knorr反应

Scheme 43. Chiral phosphoric acid catalyzed atroposelective Paal-Knorr reaction

图式44. 手性磷酸催化阻旋选择性氮环化反应

Scheme 44. Chiral phosphoric acid catalyzed atroposelective nitrogen annulation

图式45. 分子内缩合构建轴手性N-芳基苯并咪唑

Scheme 45. Construction of axial chiral N-arylbenzimidazole via intramolecular condensation

图式46. N-芳基苯并咪唑的对映选择性合成

Scheme 46. Enantioselective synthesis of N-aryl benzimidazoles

图式47. 异吲哚酮的阻旋选择性合成

Scheme 47. Atroposelective synthesis of isoindolinones

图式48. N-芳基喹唑啉酮的对映选择性合成

Scheme 48. Enantioselective synthesis of N-aryl quinazolinones

图式49. NHC催化阻旋选择性环化合成噻嗪衍生物

Scheme 49. NHC-catalyzed atroposelective annulation to thiazine derivatives

图式50. NHC催化阻旋选择性[3＋4]环加成反应

Scheme 50. NHC-catalyzed atroposelective [3＋4] annulation

图式51. N-芳基萘并咪唑阻旋选择性合成

Scheme 51. Atroposelective synthesis of N-aryl naphthoimidazole

图式52. 铑催化阻旋选择性[2＋2＋2]环加成反应

Scheme 52. Rh-catalyzed atroposelective [2＋2＋2] cycloaddition

图式53. N-芳基吲哚酮的不对称C—H键活化/环化反应

Scheme 53. Rh-catalyzed asymmetric C—H activation/cyclization reaction of N-aryl indolinone

图式54. 铑催化不对称碳氢键活化/炔胺插炔环化反应

Scheme 54. Rh-catalyzed asymmetric C—H activation/ynamine insertion annulation

图式55. 铑催化阻旋选择性Click反应

Scheme 55. Rh-catalyzed atroposelective Click reaction

图式56. 铑催化炔酰胺的阻旋选择性[2＋2＋2]环加成反应

Scheme 56. Rh-catalyzed atroposelective [2＋2＋2] cycloaddition with ynamide

图式57. 铜催化手性亚砜辅基诱导的不对称芳胺化反应

Scheme 57. Enantiopure sulfinyl iodanes induced Cu-catalyzed atroposelective aryl amination

图式58. 铜催化不对称C—N偶联反应

Scheme 58. Cu-catalyzed asymmetric C—N coupling reaction

图式59. 铱催化阻旋选择性合成烯酰胺

Scheme 59. Ir-catalyzed atroposelective synthesis of enamides

图式60. 手性磷酸催化不对称亲电胺化反应

Scheme 60. Chiral phosphoric acid-catalyzed asymmetric electrophilic amination

图式61. 芳烃的阻旋选择性胺化反应

Scheme 61. Atroposelective amination of arenes

图式62. 3-胺基吲哚的阻旋选择性合成

Scheme 62. Atroposelective synthesis of 3-amino indole

图式63. N-芳基苯醌的阻旋选择性合成

Scheme 63. Atroposelective synthesis of N-arylated quinoids

图式64. 铑催化卡宾的阻旋选择性N—H键插入反应

Scheme 64. Rh-catalyzed atroposelective N—H insertion of carbene

参考文献 66

[1]	(a) Cheng, J. K.; Xiang, S.-H.; Li, S.; Ye, L.; Tan, B. Chem. Rev. 2021, 121, 4805. doi: 10.1021/acs.chemrev.0c01306
	(b) Cheng, J. K.; Xiang, S.-H.; Tan, B. Acc. Chem. Res. 2022, 55, 2920. doi: 10.1021/acs.accounts.2c00509
	(c) Da, B.; Xiang, S.; Li, S.; Tan, B. Chin. J. Chem. 2021, 39, 1787. doi: 10.1002/cjoc.v39.7
	(d) Wang, Y.-B.; Tan, B. Acc. Chem. Res. 2018, 51, 534. doi: 10.1021/acs.accounts.7b00602
[2]	(a) Kitagawa O. Acc. Chem. Res. 2021, 54, 719. doi: 10.1021/acs.accounts.0c00767
	(b) Shi, B.-F.; Colobert, F. Chem. Catal. 2021, 1, 485.
[3]	Wu, Y.-J.; Liao, G.; Shi, B.-F. Green Synth. Catal. 2022, 3, 117.
[4]	(a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131. doi: 10.1021/ja00086a056
	(b) Duan, W.-L.; Imazaki, Y.; Shintani, R.; Hayashi, T. Tetrahedro. 2007, 63, 8529. doi: 10.1016/j.tet.2007.05.025
[5]	Wang, J.; Chen, H.; Kong, L.; Wang, F.; Lan, Y.; Li, X. ACS Catal. 2021, 11, 9151. doi: 10.1021/acscatal.1c02450
[6]	Wang, J.; Li, X. Sci. China Chem. 2023, 66, 2046. doi: 10.1007/s11426-023-1646-0
[7]	Sun, F.; Wang, T.; Cheng, G.-J.; Fang, X. ACS Catal. 2021, 11, 7578. doi: 10.1021/acscatal.1c01971
[8]	Gu, X.-W.; Sun, Y.-L.; Xie, J.-L.; Wang, X.-B.; Xu, Z.; Yin, G.-W.; Li, L.; Yang, K.-F.; Xu, L.-W. Nat. Commun. 2020, 11, 2904. doi: 10.1038/s41467-020-16716-5
[9]	Liu, H.-C.; Tao, H.-Y.; Cong, H.; Wang, C.-J. J. Org. Chem. 2016, 81, 3752. doi: 10.1021/acs.joc.6b00396
[10]	(a) Di Iorio, N.; Righi, P.; Mazzanti, A.; Mancinelli, M.; Ciogli, A.; Bencivenni, G. J. Am. Chem. Soc. 2014, 136, 10250. doi: 10.1021/ja505610k
	(b) Eudier, F.; Righi, P.; Mazzanti, A.; Ciogli, A.; Bencivenni, G. Org. Lett. 2015, 17, 1728. doi: 10.1021/acs.orglett.5b00509
	(c) Mondal, S.; Mukherjee, S. Org. Lett. 2022, 24, 8300. doi: 10.1021/acs.orglett.2c03272
[11]	(a) Di Iorio, N.; Champavert, F.; Erice, A.; Righi, P.; Mazzanti, A.; Bencivenni, G. Tetrahedro. 2016, 72, 5191. doi: 10.1016/j.tet.2016.02.052
	(b) Di Iorio, N.; Soprani, L.; Crotti, S.; Marotta, E.; Mazzanti, A.; Righi, P.; Bencivenni, G. Synthesi. 2017, 49, 1519. doi: 10.1055/s-0036-1588408
[12]	Zhang, J.; Zhang, Y.; Lin, L.; Yao, Q.; Liu, X.; Feng, X. Chem. Commun. 2015, 51, 10554. doi: 10.1039/C5CC03203B
[13]	(a) Zhuo, S.; Zhu, T.; Zhou, L.; Mou, C.; Chai, H.; Lu, Y.; Pan, L.; Jin, Z.; Chi, Y. R. Angew. Chem.. Int. Ed. 2019, 58, 1784. doi: 10.1002/anie.v58.6
	(b) Barik, S.; Shee, S.; Das, S.; Gonnade, R. G.; Jindal, G.; Mukherjee, S.; Biju, A. T. Angew. Chem.. Int. Ed. 2021, 60, 12264. doi: 10.1002/anie.v60.22
[14]	Jin, J.; Huang, X.; Xu, J.; Li, T.; Peng, X.; Zhu, X.; Zhang, J.; Jin, Z.; Chi, Y. R. Org. Lett. 2021, 23, 3991. doi: 10.1021/acs.orglett.1c01191
[15]	Zhang, J.-W.; Xu, J.-H.; Cheng, D.-J.; Shi, C.; Liu, X.-Y.; Tan, B. Nat. Commun. 2016, 7, 10677. doi: 10.1038/ncomms10677
[16]	Zhang, L.-L.; Zhang, J.-W.; Xiang, S.-H.; Guo, Z.; Tan, B. Org. Lett. 2018, 20, 6022. doi: 10.1021/acs.orglett.8b02361
[17]	Zhang, L.; Xiang, S.-H.; Wang, J.; Xiao, J.; Wang, J.-Q.; Tan, B. Nat. Commun. 2019, 10, 566. doi: 10.1038/s41467-019-08447-z pmid: 30718716
[18]	Dai, L.; Zhou, X.; Guo, J.; Dai, X.; Huang, Q.; Lu, Y. Nat. Commun. 2023, 14, 4813. doi: 10.1038/s41467-023-40491-8
[19]	Hirai, M.; Terada, S.; Yoshida, H.; Ebine, K.; Hirata, T.; Kitagawa, O. Org. Lett. 2016, 18, 5700. doi: 10.1021/acs.orglett.6b02865
[20]	(a) Diener, M. E.; Metrano, A. J.; Kusano, S.; Miller, S. J. J. Am. Chem. Soc. 2015, 137, 12369. doi: 10.1021/jacs.5b07726
	(b) Crawford, J. M.; Stone, E. A.; Metrano, A. J.; Miller, S. J.; Sigman, M. S. J. Am. Chem. Soc. 2018, 140, 868. doi: 10.1021/jacs.7b11303
[21]	Vaidya, S. D.; Toenjes, S. T.; Yamamoto, N.; Maddox, S. M.; Gustafson, J. L. J. Am. Chem. Soc. 2020, 142, 2198. doi: 10.1021/jacs.9b12994 pmid: 31944689
[22]	Kim, A.; Kim, A.; Park, S.; Kim, S.; Jo, H.; Ok, K. M.; Lee, S. K.; Song, J.; Kwon, Y. Angew. Chem.. Int. Ed. 2021, 60, 12279. doi: 10.1002/anie.v60.22
[23]	Bie, J.; Lang, M.; Wang, J. Org. Lett. 2018, 20, 5866. doi: 10.1021/acs.orglett.8b02538
[24]	(a) Kitagawa, O.; Kohriyama, M.; Taguchi, T. J. Org. Chem. 2002, 67, 8682. pmid: 31117580
	(b) Kitagawa, O.; Takahashi, M.; Kohriyama, M.; Taguchi, T. J. Org. Chem. 2003, 68, 9851. pmid: 31117580
	(c) Liu, Y.; Feng, X.; Du, H. Org. Biomol. Chem. 2015, 13, 125. doi: 10.1039/C4OB01087F pmid: 31117580
	(d) Kikuchi, Y.; Nakamura, C.; Matsuoka, M.; Asami, R.; Kitagawa, O. J. Org. Chem. 2019, 84, 8112. doi: 10.1021/acs.joc.9b00989 pmid: 31117580
	(e) Gao, Z.; Yan, C.-X.; Qian, J.; Yang, H.; Zhou, P.; Zhang, J.; Jiang, G. ACS Catal. 2021, 11, 6931. doi: 10.1021/acscatal.1c01345 pmid: 31117580
[25]	Li, S.-L.; Yang, C.; Wu, Q.; Zheng, H.-L.; Li, X.; Cheng, J.-P. J. Am. Chem. Soc. 2018, 140, 12836. doi: 10.1021/jacs.8b06014
[26]	Yang, G.-H.; Zheng, H.; Li, X.; Cheng, J.-P. ACS Catal. 2020, 10, 2324. doi: 10.1021/acscatal.9b05443
[27]	(a) Kitagawa, O.; Takahashi, M.; Yoshikawa, M.; Taguchi, T. J. Am. Chem. Soc. 2005, 127, 3676. pmid: 17002389
	(b) Kitagawa, O.; Yoshikawa, M.; Tanabe, H.; Morita, T.; Takahashi, M.; Dobashi, Y.; Taguchi, T. J. Am. Chem. Soc. 2006, 128, 12923. pmid: 17002389
	(c) 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. doi: 10.1039/D1QO01147B pmid: 17002389
[28]	(a) Li, D.; Wang, S.; Ge, S.; Dong, S.; Feng, X. Org. Lett. 2020, 22, 5331. doi: 10.1021/acs.orglett.0c01581
	(b) Ong, J.-Y.; Ng, X. Q.; Lu, S.; Zhao, Y. Org. Lett. 2020, 22, 6447. doi: 10.1021/acs.orglett.0c02266
[29]	Shirakawa, S.; Liu, K.; Maruoka, K. J. Am. Chem. Soc. 2012, 134, 916. doi: 10.1021/ja211069f pmid: 22208662
[30]	(a) Yao, Q.-J.; Xie, P.-P.; Wu, Y.-J.; Feng, Y.-L.; Teng, M.-Y.; Hong, X.; Shi, B.-F. J. Am. Chem. Soc. 2020, 142, 18266. doi: 10.1021/jacs.0c09400
	(b) Jia, Z.-S.; Wu, Y.-J.; Yao, Q.-J.; Xu, X.-T.; Zhang, K.; Shi, B.-F. Org. Lett. 2022, 24, 304. doi: 10.1021/acs.orglett.1c03967
	(c) Wu, Y.-J.; Xie, P.-P.; Zhou, G.; Yao, Q.-J.; Hong, X.; Shi, B.-F. Chem. Sci. 2021, 12, 9391. doi: 10.1039/D1SC01130H
[31]	Zhang, S.; Yao, Q.-J.; Liao, G.; Li, X.; Li, H.; Chen, H.-M.; Hong, X.; Shi, B.-F. ACS Catal. 2019, 9, 1956. doi: 10.1021/acscatal.8b04870
[32]	(a) Zhang, J.; Xu, Q.; Wu, J.; Fan, J.; Xie, M. Org. Lett. 2019, 21, 6361. doi: 10.1021/acs.orglett.9b02243
	(b) Dhawa, U.; Wdowik, T.; Hou, X.; Yuan, B.; Oliveira, J. C. A.; Ackermann, L. Chem. Sci. 2021, 12, 14182. doi: 10.1039/D1SC04687J
[33]	Wang, L.; Yuan, W.; Wang, Z.; Luo, J.; Zhou, T.; Shi, B. Chin. J. Chem. 2023, 41, 2788. doi: 10.1002/cjoc.v41.21
[34]	Mi, R.; Ding, Z.; Yu, S.; Crabtree, R. H.; Li, X. J. Am. Chem. Soc. 2023, 145, 8150. doi: 10.1021/jacs.3c01162
[35]	(a) Takahashi, I.; Morita, F.; Kusagaya, S.; Fukaya, H.; Kitagawa, O. Tetrahedron: Asymmetry 2012, 23, 1657.
	(b) Hirata, T.; Takahashi, I.; Suzuki, Y.; Yoshida, H.; Hasegawa, H.; Kitagawa, O. J. Org. Chem. 2016, 81, 318. doi: 10.1021/acs.joc.5b02387
	(c) Zhang, P.; Wang, X.; Xu, Q.; Guo, C.; Wang, P.; Lu, C.; Liu, R. Angew. Chem.. Int. Ed. 2021, 60, 21718. doi: 10.1002/anie.v60.40
	(d) Zhang, P.; Guo, C.-Q.; Yao, W.; Lu, C.-J.; Li, Y.; Paton, R. S.; Liu, R.-R. ACS Catal. 2023, 13, 7680. doi: 10.1021/acscatal.3c00732
[36]	Fan, X.; Zhang, X.; Li, C.; Gu, Z. ACS Catal. 2019, 9, 2286. doi: 10.1021/acscatal.8b04789
[37]	Liu, Z.-S.; Xie, P.-P.; Hua, Y.; Wu, C.; Ma, Y.; Chen, J.; Cheng, H.-G.; Hong, X.; Zhou, Q. Che. 2021, 7, 1917.
[38]	(a) Ototake, N.; Morimoto, Y.; Mokuya, A.; Fukaya, H.; Shida, Y.; Kitagawa, O. Chem.-Eur. J. 2010, 16, 6752. doi: 10.1002/chem.v16:23
	(b) Wang, Z.; Zhu, L.; Li, C.; Liu, B.; Hong, X.; Ye, L. Angew. Chem.. Int. Ed. 2022, 61, e202201436.
[39]	Liu, H.; Feng, W.; Kee, C. W.; Leow, D.; Loh, W.-T.; Tan, C.-H. Adv. Synth. Catal. 2010, 352, 3373. doi: 10.1002/adsc.v352.18
[40]	Mishra, K.; Guyon, D.; San Martin, J.; Yan, Y. J. Am. Chem. Soc. 2023, 145, 17242. doi: 10.1021/jacs.3c04593
[41]	Arunachalampillai, A.; Chandrappa, P.; Cherney, A.; Crockett, R.; Doerfler, J.; Johnson, G.; Kommuri, V. C.; Kyad, A.; McManus, J.; Murray, J.; Myren, T.; Fine Nathel, N.; Ndukwe, I.; Ortiz, A.; Reed, M.; Rui, H.; Silva Elipe, M. V.; Tedrow, J.; Wells, S.; Yacoob, S.; Yamamoto, K. Org. Lett. 2023, 25, 5856. doi: 10.1021/acs.orglett.3c02117
[42]	Sun, L.; Chen, H.; Liu, B.; Chang, J.; Kong, L.; Wang, F.; Lan, Y.; Li, X. Angew. Chem.. Int. Ed. 2021, 60, 8391. doi: 10.1002/anie.v60.15
[43]	Wang, P.; Wu, H.; Zhang, X.-P.; Huang, G.; Crabtree, R. H.; Li, X. J. Am. Chem. Soc. 2023, 145, 8417.
[44]	Wang, B.; Xu, G.; Huang, Z.; Wu, X.; Hong, X.; Yao, Q.; Shi, B. Angew. Chem.. Int. Ed. 2022, 61, e202208912.
[45]	Zhang, L.; Zhang, J.; Ma, J.; Cheng, D.-J.; Tan, B. J. Am. Chem. Soc. 2017, 139, 1714. doi: 10.1021/jacs.6b09634 pmid: 28106384
[46]	Wang, L.; Zhong, J.; Lin, X. Angew. Chem.. Int. Ed. 2019, 58, 15824. doi: 10.1002/anie.v58.44
[47]	(a) Kwon, Y.; Chinn, A. J.; Kim, B.; Miller, S. J. Angew. Chem.. Int. Ed. 2018, 57, 6251. doi: 10.1002/anie.v57.21
	(b) Kwon, Y.; Li, J.; Reid, J. P.; Crawford, J. M.; Jacob, R.; Sigman, M. S.; Toste, F. D.; Miller, S. J. J. Am. Chem. Soc. 2019, 141, 6698. doi: 10.1021/jacs.9b01911
[48]	Man, N.; Lou, Z.; Li, Y.; Yang, H.; Zhao, Y.; Fu, H. Org. Lett. 2020, 22, 6382. doi: 10.1021/acs.orglett.0c02214
[49]	Min, C.; Lin, Y.; Seidel, D. Angew. Chem.. Int. Ed. 2017, 56, 15353. doi: 10.1002/anie.v56.48
[50]	Wang, Y.-B.; Zheng, S.-C.; Hu, Y.-M.; Tan, B. Nat. Commu. 2017, 8, 15489.
[51]	Li, T.; Mou, C.; Qi, P.; Peng, X.; Jiang, S.; Hao, G.; Xue, W.; Yang, S.; Hao, L.; Chi, Y. R.; Jin, Z. Angew. Chem.. Int. Ed. 2021, 60, 9362. doi: 10.1002/anie.v60.17
[52]	Wang, L.; Li, S.; Blümel, M.; Philipps, A. R.; Wang, A.; Puttreddy, R.; Rissanen, K.; Enders, D. Angew. Chem.. Int. Ed. 2016, 55, 11110. doi: 10.1002/anie.v55.37
[53]	An, Q.; Xia, W.; Ding, W.; Liu, H.; Xiang, S.; Wang, Y.; Zhong, G.; Tan, B. Angew. Chem.. Int. Ed. 2021, 60, 24888. doi: 10.1002/anie.v60.47
[54]	Augé, M.; Feraldi-Xypolia, A.; Barbazanges, M.; Aubert, C.; Fensterbank, L.; Gandon, V.; Kolodziej, E.; Ollivier, C. Org. Lett. 2015, 17, 3754. doi: 10.1021/acs.orglett.5b01738
[55]	Li, H.; Yan, X.; Zhang, J.; Guo, W.; Jiang, J.; Wang, J. Angew. Chem.. Int. Ed. 2019, 58, 6732. doi: 10.1002/anie.v58.20
[56]	(a) Wang, F.; Jing, J.; Zhao, Y.; Zhu, X.; Zhang, X.; Zhao, L.; Hu, P.; Deng, W.; Li, X. Angew. Chem.. Int. Ed. 2021, 60, 16628. doi: 10.1002/anie.v60.30
	(b) Wang, P.; Huang, Y.; Jing, J.; Wang, F.; Li, X. Org. Lett. 2022, 24, 2531. doi: 10.1021/acs.orglett.2c00686
	(c) Zhu, X.; Mi, R.; Yin, J.; Wang, F.; Li, X. Chem. Sci. 2023, 14, 7999. doi: 10.1039/D3SC02714G
[57]	Zhou, L.; Li, Y.; Li, S.; Shi, Z.; Zhang, X.; Tung, C.-H.; Xu, Z. Chem. Sci. 2023, 14, 5182. doi: 10.1039/d3sc00610g pmid: 37206396
[58]	(a) Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586. pmid: 17764192
	(b) Oppenheimer, J.; Hsung, R. P.; Figueroa, R.; Johnson, W. L. Org. Lett. 2007, 9, 3969. pmid: 17764192
	(c) Oppenheimer, J.; Johnson, W. L.; Figueroa, R.; Hayashi, R.; Hsung, R. P. Tetrahedro. 2009, 65, 5001. doi: 10.1016/j.tet.2009.03.078 pmid: 17764192
[59]	Rae, J.; Frey, J.; Jerhaoui, S.; Choppin, S.; Wencel-Delord, J.; Colobert, F. ACS Catal. 2018, 8, 2805. doi: 10.1021/acscatal.7b04343
[60]	Frey, J.; Malekafzali, A.; Delso, I.; Choppin, S.; Colobert, F.; Wencel-Delord, J. Angew. Chem.. Int. Ed. 2020, 59, 8844. doi: 10.1002/anie.v59.23
[61]	(a) Sun, C.; Qi, X.; Min, X.-L.; Bai, X.-D.; Liu, P.; He, Y. Chem. Sci. 2020, 11, 10119. doi: 10.1039/D0SC02828B
	(b) Zhang, X.; Gu, J.; Cui, W.; Ye, Z.; Yi, W.; Zhang, Q.; He, Y. Angew. Chem.. Int. Ed. 2022, 61, e202210456.
	(c) Zou, J.; Yang, Y.; Gu, J.; Liu, F.; Ye, Z.; Yi, W.; He, Y. Angew. Chem.. Int. Ed. 2023, 62, e202310320.
	(d) Wu, Y.-X.; Liu, Q.; Zhang, Q.; Ye, Z.; He, Y. Cell Rep. Phys. Sci. 2022, 3, 101005.
	(e) Zhang, X.-L.; Qi, X.; Wu, Y.-X.; Liu, P.; He, Y. Cell Rep. Phys. Sci. 2021, 2, 100594.
[62]	(a) Brandes, S.; Bella, M.; Kjærsgaard, A.; Jørgensen, K.A. Angew. Chem.. Int. Ed. 2006, 118, 1165. doi: 10.1002/ange.v118:7
	(b) Bai, H.-Y.; Tan, F.-X.; Liu, T.-Q.; Zhu, G.-D.; Tian, J.-M.; Ding, T.-M.; Chen, Z.-M.; Zhang, S.-Y. Nat. Commun. 2019, 10, 3063. doi: 10.1038/s41467-019-10858-x
[63]	Xia, W.; An, Q.; Xiang, S.; Li, S.; Wang, Y.; Tan, B. Angew. Chem.. Int. Ed. 2020, 59, 6775. doi: 10.1002/anie.v59.17
[64]	Qin, J.; Zhou, T.; Zhou, T.; Tang, L.; Zuo, H.; Yu, H.; Wu, G.; Wu, Y.; Liao, R.; Zhong, F. Angew. Chem.. Int. Ed. 2022, 61, e202205159.
[65]	Guo, C.; Lu, C.; Zhan, L.; Zhang, P.; Xu, Q.; Feng, J.; Liu, R. Angew. Chem.. Int. Ed. 2022, 61, e202212846.
[66]	(a) Ren, Q.; Cao, T.; He, C.; Yang, M.; Liu, H.; Wang, L. ACS Catal. 2021, 11, 6135. doi: 10.1021/acscatal.1c01232
	(b) Niu, C.; Zhou, Y.; Chen, Q.; Zhu, Y.; Tang, S.; Yu, Z.-X.; Sun, J. Org. Lett. 2022, 24, 7428. doi: 10.1021/acs.orglett.2c03003