可见光促进的烯烃合成研究进展

doi:10.6023/cjoc202208044

摘要/Abstract

烯烃及其功能化衍生物是有机合成中最基本的合成砌块之一, 同时也普遍存在于许多天然产物和功能材料中. 传统的合成方法包括Wittig烯烃化、Peterson烯烃化、Horner-Wadsworth-Emmons反应等, 这些反应已经成为教科书中的经典反应, 为烯烃的高效合成提供了诸多选择. 这些方法大多基于离子型的反应路径, 并且有些方法需要在形成 C—C双键的位点对起始原料进行预官能化, 导致反应效率和选择性较低. 可见光光氧化还原催化因其符合绿色化学要求, 以及大多涉及自由基中间体的独特反应机理模式, 近年来已逐步成为化学家们发展新颖合成方法学的重要平台. 主要介绍近年来在光化学合成烯烃方面的进展, 并对该领域的发展方向进行了展望.

关键词: 可见光, 光氧化还原催化, 自由基反应, 烯烃合成

Alkenes and their functionalized derivatives represent a versatile class of building blocks in organic synthesis. The traditional synthetic methods include Wittig oleﬁnation, Peterson oleﬁnation, Horner-Wadsworth-Emmons reaction and others, and many of these classic reactions have also become textbook knowledge. Most of these methods are based on ionic pathways and some still require pre-functionalization at the sites where C—C double bonds are formed, resulting some limitations on substrate scope or functional group tolerance. Over the past few years, photoredox catalysis has become a powerful platform for new reaction design owing to its green chemistry characteristics and unique activation modes. The recently developed and representative methods for the synthesis of alkenes under photochemical conditions are summarized. Moreover, the prospects of further developments are also discussed.

Key words: visible light, photoredox catalysis, radical reaction, alkene synthesis

引用此文

高盼盼, 肖文精, 陈加荣. 可见光促进的烯烃合成研究进展[J]. 有机化学, 2022, 42(12): 3923-3943.

Pan-Pan Gao, Wen-Jing Xiao, Jia-Rong Chen. Recent Progresses in Visible-Light-Driven Alkene Synthesis[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 3923-3943.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 57

图式1. 合成烯烃的策略

Scheme 1. General strategies to access alkenes (a) Traditional methods to construct alkenes; (b) photoredox catalytic synthesis of alkenes

图式2. 烯基卤代物与羧酸的脱羧交叉偶联反应

Scheme 2. Decarboxylative cross-coupling of carboxylic acids with vinyl halides

图式3. 烯基卤代物与羧酸脱羧烯烃化反应机理

Scheme 3. Mechanism for decarboxylative olefination of carboxylic acids with vinyl halides

图式4. 乙烯基砜与三级胺的烯烃化反应及反应机理

Scheme 4. Plausible mechanism for the radical addition between vinyl sulfones and tertiary amines

图式5. 光诱导脂肪酸和末端烯烃的脱羧Heck型偶联

Scheme 5. Photo-induced decarboxylative Heck-type coupling reaction of aliphatic acids and terminal alkenes

图式6. N-(酰氧基)邻苯二甲酰亚胺与(杂)芳基烯烃的脱羧Heck偶联反应

Scheme 6. Decarboxylative Heck reaction of (hetero)arylalkenes with aliphatic N-(acyloxy)phthalimides

图式7. 光诱导羧酸与β-芳基卤代乙烯的交叉偶联反应

Scheme 7. Photo-induced cross coupling reactions of carboxylic acids with β-aryl-vinyl halides

图式8. 光诱导芳基羧酸和烯基三氟甲磺酸酯的烯烃化反应

Scheme 8. Photo-induced alkenylation of aryl carboxylic acids and alkenyl triflates

图式9. 光诱导硼酸盐与烯基羧酸的偶联反应

Scheme 9. Photo-induced coupling reaction of borates with alkenyl carboxylic acids

图式10. 光催化/铜双催化α,β-不饱和羧酸的脱羧二氟乙酰化反应

Scheme 10. Photoredox/copper catalyzed decarboxylation difluoroacetylation of α,β-unsaturated carboxylic acids

图式11. 光诱导芳基烯烃与卤代烃的偶联反应

Scheme 11. Photo-induced coupling reaction of arylalkenes with halogenated hydrocarbons

图式12. 光诱导烯基卤化物与4-烷基-1,4-二氢吡啶的交叉偶联反应

Scheme 12. Photo-induced cross-coupling of alkenyl halides with 4-alkyl-1,4-dihydropyridines

图式13. 光诱导三苯基吡啶鎓盐与烯基砜的偶联反应

Scheme 13. Photo-induced coupling reaction of triphenylpyridinium salts with vinyl sulfones

图式14. 光催化烷基溴代物与烯基砜的偶联反应

Scheme 14. Photocatalytic coupling of alkyl bromides and alkenyl sulfones

图式15. 光催化烷基硼酸与芳基烯基砜的偶联反应

Scheme 15. Photocatalytic coupling reaction of alkyl boronic acids with arylalkenyl sulfones

图式16. 光诱导苄基硫盐与芳基烯烃的偶联反应

Scheme 16. Photo-induced coupling reaction of benzyl sulfonium salts with aryl alkenes

图式17. 光诱导四氢呋喃与炔烃的烯基化反应

Scheme 17. Photo-induced vinylation of tetrahydrofuran with alkynes

图式18. 光诱导烷基二酰基过氧化物对末端芳基炔烃的加氢烷基化

Scheme 18. Photo-induced hydroalkylation of terminal aryl alkynes with alkyl diacyl peroxides

图式19. 光诱导与炔丙醇和重氮盐的交叉偶联

Scheme 19. Photo-induced cross-coupling reaction of propargyl alcohols and diazonium salts

图式20. 光诱导协同镍催化的内炔烃与醚和酰胺α-杂 C(sp3)—H键的加氢烷基化反应

Scheme 20. Photo-induced nickel-catalyzed hydroalkylation of internal alkynes with ether and amide α-hetero C(sp3)—H bonds

图式21. 光催化的炔烃与芳基亚磺酸的偶联反应

Scheme 21. Photocatalytic coupling reaction of alkynes with aryl sulfonic acids

图式22. 光氧化还原催化和镍催化协同催化的末端炔烃的烷基芳基化

Scheme 22. Alkylarylation of terminal alkynes by dual photoredox and nickel catalysis

图式23. 光氧化还原催化肟和末端炔烃开环乙烯基化反应

Scheme 23. Photoredox catalysis ring-opening-vinylation of oxime and terminal alkynes

图式24. 光诱导烷基吡啶盐与末端芳炔的脱氨基偶联

Scheme 24. Photoinduced deaminative coupling of alkylpyridium salts with terminal arylalkynes

图式25. 光诱导N-芳基四氢异喹啉和烯丙基衍生物的交叉偶联反应

Scheme 25. Photo-induced cross-coupling with N-aryltetrahydroisoquinolines and allyl derivatives

图式26. α-氨基和苯乙酸烯丙酯的双催化脱羧烯丙基化

Scheme 26. Decarboxylative alylation of α-amino and phenylacetic allyl esters via dual catalysis

图式27. α-氨基酸的双催化脱羧烯丙基化

Scheme 27. Decarboxylative allylations of α-amino acids by dual photoredox/palladium catalysis

图式28. 光诱导高价双邻苯二酚硅化合物作为烷基自由基前体参与的偶联反应

Scheme 28. Photo-induced coupling reactions of high-valent biquinol-silicon compounds as alkyl radical precursors

图式29. 光催化4-烷基-1,4-二氢吡啶和烯丙酯的烯丙基烷基化

Scheme 29. Photocatalytic allyl alkylation of 4-alkyl-1,4-dihydropyridines and allyl esters

图式30. 光氧化还原和镍双催化醛的烯丙基化反应

Scheme 30. Allylation of aldehydes by dual photoredox and nickel catalysis

图式31. 有机光氧化还原促进的钴催化烯丙基烷基化

Scheme 31. Cobalt-catalyzed allylic alkylation enabled by organophotoredox catalysis

图式32. 钴和光氧化还原催化烯丙基烷基化的反应机理

Scheme 32. Proposed mechanism for the allylic alkylation with cobalt and photoredox catalysis.

图式33. 钴和有机光氧化还原协同催化的脂肪胺区域选择性脱氨基烯丙基化

Scheme 33. Regioselective deaminative allylation of aliphatic amines via dual cobalt and organophotoredox catalysis

图式34. 光催化羧酸脱氢烯化反应

Scheme 34. Photocatalytic dehydrogenative decarboxyolefination of carboxylic acids

图式35. 光催化羧酸的脱氢脱羧烯化反应机理

Scheme 35. Proposed mechanism for photocatalytic dehydrogenative decarboxyolefination of carboxylic acids

图式36. 光氧化还原/钴双催化的N-酰基氨基酸的脱羧消除

Scheme 36. Dual photoredox/cobalt dual catalyzed decarboxylative elimination of N-acyl amino acids

图式37. 有机光氧化还原/铜催化实现活化脂肪酸的脱羧烯化

Scheme 37. Decarboxylative ole?nation of activated aliphatic acids enabled by dual organophotoredox/copper catalysis

图式38. 活化脂肪酸脱羧烯化的反应机理

Scheme 38. Proposed mechanism for decarboxylative ole?nation of activated aliphatic acids

图式39. 光催化协同酶催化的羧酸的脱羧/脱氢合成烯烃

Scheme 39. Dehydrodecarboxylation ole?nation of carboxylic acids by dual photoredox/enzyme catalysis

图式40. 光协同铁催化的环状叔羧酸的脱羧烯基化反应

Scheme 40. Decarboxyalkenylation of cyclic tertiary carboxylic acids by dual photoredox/iron catalysis

图式41. 可见光催化环烷烃的脱氢烯烃化反应

Scheme 41. Visible light-catalyzed dehydroolefination of naphthenes

图式42. 可见光诱导α-氨基烷基自由基和钴催化介导的卤原子转移合成烯烃化合物

Scheme 42. Visible light-induced α-aminoalkyl radicals and cobalt-catalyzed halogen transfer to synthesize alkenes

图式43. 通过XAT和光氧化还原-钴双催化的E2消除机理

Scheme 43. Proposed mechanism for E2 elimination via XAT and dual photoredox-cobalt catalysis

图式44. 有机光氧化还原/钴双催化的脂肪族化合物的位点选择性脱氢

Scheme 44. Site-selective dehydrogenation of aliphatics enabled by organophotoredox/cobalt dual catalysis

图式45. 有机光氧化还原/钴双催化的脂肪族烷烃脱氢反应机理

Scheme 45. Proposed mechanism for dehydrogenation of aliphatics enabled by organophotoredox/cobalt dual catalysis

图式46. 光诱导钯催化下的脂肪醇C—H官能化

Scheme 46. Photoinduced Pd-catalyzed silyl ethers into silyl enol ethers

图式47. 光诱导钯催化下的脂肪醇C—H官能化

Scheme 47. Photoinduced Pd-catalyzed C—H functionalization of aliphatic alcohols

图式48. 光诱导钯催化下的脂肪胺去饱和化合成烯烃

Scheme 48. Photoinduced Pd-catalyzed for desaturation of aliphatic amines for alkene synthesis

图式49. 光诱导酰胺衍生物的脱氢烯化反应

Scheme 49. Photoinduced dehydroalkenylation of amide derivatives

图式50. 光诱导钴催化下的化学选择性脱氢

Scheme 50. Photoinduced cobalt-catalyzed chemoselective dehydrogenation

图式51. 光氧化还原/钴肟双催化实现无受体脱氢反应构建烯烃

Scheme 51. Photoredox/cobaloxime dual catalyzed and acceptorless dehydrogenation for the construction of alkenes

图式52. 可见光催化芳基重氮乙酸酯和重氮羰基化合物的交叉偶联

Scheme 52. Visible-light-promoted cross-coupling of aryldiazoacetates and diazocarbonyls

图式53. 光氧化还原催化芳族醛的脱氧还原烯烃化

Scheme 53. Deoxygenative reductive olefination of aromatic aldehydes via photoredox catalysis

图式54. 通过光氧化还原催化吡啶的支链选择性烯基化反应

Scheme 54. Branch-selective alkenylation of pyridines via photoredox catalysis

图式55. 可见光促进的芳基重氮乙酸酯与硫叶立德的偶联

Scheme 55. Visible light-promoted coupling of aryldiazoacetates to sulfur ylides

图式56. 可见光促进的硫叶立德和N-对甲苯磺酰腙的Photo- Wolff-Kischner反应合成烯烃

Scheme 56. Alkene synthesis by visible-light-driven photo- Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones

图式57. 电介导光氧化还原催化次膦醇的C(sp3)—O选择性裂解合成烯烃

Scheme 57. Electro-mediated photoredox catalysis for selective C(sp3)—O cleavages of phosphinated alcohols for alkene synthesis

参考文献 77

[1]	Domski, G. J.; Rose, J. M.; Coates, G. W.; Bolig, A. D.; Brookhart, M. Prog. Polym. Sci. 2007, 32, 30. doi: 10.1016/j.progpolymsci.2006.11.001
[2]	Álvarez, R.; Vaz, B.; Gronemeyer, H.; de Lera, A. R. Chem. Rev. 2014, 114, 1. doi: 10.1021/cr400126u pmid: 24266866
[3]	Hassam, M.; Taher, A.; Arnott, G. E.; Green, I. R.; van Otterlo, W. A. L. Chem. Rev. 2015, 115, 5462. doi: 10.1021/acs.chemrev.5b00052
[4]	(a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. doi: 10.1021/cr00094a007 pmid: 20000700
	(b) Chang, H.; Jayanth, T. T.; Wang, C.; Cheng, C. J. Am. Chem. Soc. 2007, 129, 12032. doi: 10.1021/ja073604c pmid: 20000700
	(c) van Staden, L. F.; Gravestock, D.; Ager, D. J. Chem. Rev. 2002, 31, 195. pmid: 20000700
	(d) Grubbs, R. H.; Burk, P. L.; Carr, D. D. J. Am. Chem. Soc. 1975, 97, 3265. doi: 10.1021/ja00844a082 pmid: 20000700
	(e) Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746. doi: 10.1021/cr9002424 pmid: 20000700
[5]	(a) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J.-Q. Chem. Rev. 2017, 117, 8754. doi: 10.1021/acs.chemrev.6b00622
	(b) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem. Int. Ed. 2009, 48, 5094. doi: 10.1002/anie.200806273
	(c) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Rev. 2011, 40, 5068.
[6]	(a) Godula, K.; Sames, D. Science 2006, 312, 67. pmid: 16601184
	(b) Baudoin, O. Angew. Chem., Int. Ed. 2007, 46, 1373. doi: 10.1002/anie.200604494 pmid: 16601184
	(c) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., nt. Ed. 2009, 48, 5094. pmid: 16601184
[7]	(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
	(b) Chang, L.; An, Q.; Duan, L.F.; Feng, K.-X.; Zuo, Z.-W. Chem. Rev. 2022, 122, 2429. doi: 10.1021/acs.chemrev.1c00256
	(c) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. doi: 10.1021/acs.chemrev.0c00030
	(d) Wang, P.-Z.; Zhao, Q.-Q.; Xiao, W.-J.; Chen, J.-R. Green Synth. Catal. 2020, 1, 42.
[8]	(a) Xuan, J.; Zhang, Z. -, G.; Xiao, W.-J. Angew. Chem. Int. Ed. 2015, 54, 15632. doi: 10.1002/anie.201505731 pmid: 26509837
	(b) Gooßen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem. Int. Ed. 2008, 47, 3043. doi: 10.1002/anie.200705127 pmid: 26509837
[9]	(a) Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257. doi: 10.1021/ja501621q
	(b) Chu, L.; Ohta, C.; Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 10886. doi: 10.1021/ja505964r
	(c) Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034. doi: 10.1021/ja301553c
[10]	McCarver, Stefan, J.; Noble, A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 624. doi: 10.1021/ja511913h pmid: 25521443
[11]	Noble, A.; MacMillan, D. W. J. Am. Chem. Soc. 2014, 136, 11602. doi: 10.1021/ja506094d pmid: 25026314
[12]	Heitz, D. R.; Rizwan, K.; Molander, G. A. J. Org. Chem. 2016, 81, 7308. doi: 10.1021/acs.joc.6b01207 pmid: 27336284
[13]	Cao, H.; Jiang, H.; Feng, H.; Kwan, J. M. C.; Liu, X.; Wu, J. J. Am. Chem. Soc. 2018, 140, 16360. doi: 10.1021/jacs.8b11218
[14]	Wang, G.-Z.; Shang, R.; Fu, Y. Org. Lett. 2018, 20, 888. doi: 10.1021/acs.orglett.8b00023
[15]	Huang, H.; Zhang, Y.; Ji, P.; Mariano, P. S.; Wang, W. Green Synth. Catal. 2021, 2, 27.
[16]	Li, Y.; Shao, Q.; He, H.; Zhu, C.-J.; Xue, X.-S; Xie, J. Nat. Commun. 2022, 13, 10. doi: 10.1038/s41467-021-27507-x
[17]	Darses, S.; Genet, J.-P. Chem. Rev. 2008, 108, 288. doi: 10.1021/cr0509758
[18]	(a) Sorin, G.; Martinez Mallorquin, R.; Contie, Y.; Baralle, A.; Malacria, M.; Goddard, J.-P.; Fensterbank, L. Angew. Chem., Int. Ed. 2010, 49, 8721. doi: 10.1002/anie.201004513 pmid: 21341741
	(b) Fujiwara, Y.; Domingo, V.; Seiple, I. B.; Gianatassio, R.; Del Bel, M.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 3292. doi: 10.1021/ja111152z pmid: 21341741
[19]	Huang, H.; Jia, K.; Chen, Y. Angew. Chem. Int. Ed. 2015, 54, 1881. doi: 10.1002/anie.201410176
[20]	Zhang, H.-R.; Chen, D.-Q.; Han, Y.-P.; Qiu, Y.-F.; Jin, D.-P.; Liu, X.-Y. Chem. Commun. 2016, 52, 11827. doi: 10.1039/C6CC06284A
[21]	Wang, G.-Z.; Shang, R.; Cheng, W.-M.; Fu, Y. J. Am. Chem. Soc. 2017, 139, 18307. doi: 10.1021/jacs.7b10009
[22]	Nakajima, K.; Guo, X.; Nishibayashi, Y. Chem. Asian J. 2018, 13, 3653. doi: 10.1002/asia.201801542
[23]	(a) Rössler, S. L.; Jelier, B. J.; Magnier, E.; Dagousset, G.; Carreira, E. M.; Togni, Angew. Chem. Int. Ed. 2020, 59, 9264. doi: 10.1002/anie.201911660 pmid: 31600423
	(b) Wang, Y.; Bao, Y.; Tang, M.; Ye, Z.; Yuan, Z.; Zhu, G. Chem. Commun. 2022, 58, 3847. doi: 10.1039/D2CC00369D pmid: 31600423
[24]	Ociepa, M.; Turkowska, J.; Gryko, D. ACS Catal. 2018, 8, 11362. doi: 10.1021/acscatal.8b03437
[25]	Zhou, Q.-Q.; Düsel, S. J. S.; Lu, L.-Q.; König, B.; Xiao, W.-J. Chem. Commun. 2019, 55, 107. doi: 10.1039/C8CC08362B
[26]	Yue, F.; Dong, J.; Liu, Y.; Wang, Q. Org. Lett. 2021, 23, 2477. doi: 10.1021/acs.orglett.1c00399
[27]	Otsuka, S.; Nogi, K.; Rovis, T.; Yorimitsu, H. Chem. Asian J. 2019, 14, 532. doi: 10.1002/asia.201801732
[28]	Li, J.; Zhang, J.; Tan, H.; Wang, D. Z. Org. Lett. 2015, 17, 2522. doi: 10.1021/acs.orglett.5b01053
[29]	Li, Y.; Ge, L.; Qian, B.; Babu, K. R.; Bao, H. Tetrahedron Lett. 2016, 57, 5677. doi: 10.1016/j.tetlet.2016.11.020
[30]	Um, J.; Yun, H.; Shin, S. Org. Lett. 2016, 18, 484. doi: 10.1021/acs.orglett.5b03531
[31]	Tlahuext-Aca, A. M.; Hopkinson, N. R.; Garza-Sanchez, A.; Glorius, F. Chem. Eur. J. 2016, 22, 5909. doi: 10.1002/chem.201600710
[32]	Alcaide, B.; Almendros, P.; Busto, E.; Luna, A. Adv. Synth. Catal. 2016, 358, 1526. doi: 10.1002/adsc.201600158
[33]	Deng, H. P.; Fan, X. Z.; Chen, Z. H.; Xu, Q. H.; Wu, J. J. Am. Chem. Soc. 2017, 139, 13579. doi: 10.1021/jacs.7b08158
[34]	Wang, H.; Lu, Q.; Chiang, C.-W.; Luo, Y.; Zhou, J.; Wang, G.; Lei, A. Angew. Chem., Int. Ed. 2017, 56, 595. doi: 10.1002/anie.201610000
[35]	Guo, L.; Song, F.; Zhu, S.; Li, H.; Chu, L. Nat. Commun. 2018, 9, 4543. doi: 10.1038/s41467-018-06904-9
[36]	Dauncey, E. M.; Dighe, S. U.; Douglas, J. J.; Leonori, D. Chem. Sci. 2019, 10, 7728. doi: 10.1039/C9SC02616A
[37]	Lai, S.-Z.; Yang, Y.-M.; Xu, H.; Tang, Z.-Y.; Luo, Z. J. Org. Chem. 2020, 85, 15638. doi: 10.1021/acs.joc.0c01928
[38]	Xuan, J.; Zeng, T. -T.; Feng, Z. -J.; Deng, Q. H.; Chen, J. -R.; Lu, L.-Q.; Xiao, W.-J.; Alper, H. Angew. Chem. Int. Ed. 2015, 54, 1625. doi: 10.1002/anie.201409999 pmid: 25504920
[39]	Lang, S. B.; O’Nele, K. M.; Tunge, J. A. J. Am. Chem. Soc. 2014, 136, 13606. doi: 10.1021/ja508317j
[40]	Lang, S. B.; O'Nele, K. M.; Douglas, J. T.; Tunge, J. A. Chem. Eur. J. 2015, 21, 18589. doi: 10.1002/chem.201503644
[41]	Corcé, V.; Chamoreau, L.-M.; Derat, E.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Angew. Chem. Int. Ed. 2015, 54, 11414. doi: 10.1002/anie.201504963
[42]	Zhang, H.-H.; Zhao, J.-J.; Yu, S. J. Am. Chem. Soc. 2018, 140, 16914. doi: 10.1021/jacs.8b10766
[43]	Gualandi, A.; Rodeghiero, G.; Faraone, A.; Patuzzo, F.; Marchini, M.; Calogero, F.; Perciaccante, R.; Jansen, T. P.; Ceroni, P.; Cozzi, P. G. Chem. Commun. 2019, 55, 6838. doi: 10.1039/C9CC03344K
[44]	Takizawa, K.; Sekino, T.; Sato, S.; Yoshino, T.; Kojima, M.; Matsunaga, S. Angew. Chem. Int. Ed. 2019, 58, 9199. doi: 10.1002/anie.201902509 pmid: 30998841
[45]	Zhang, M.-M.; Liu, F. Org. Chem. Front. 2018, 5, 3443. doi: 10.1039/C8QO01046C
[46]	Wu, J.; Grant, P. S.; Li, X.; Noble, A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2019, 58, 5697. doi: 10.1002/anie.201814452
[47]	Lübbesmeyer, M.; Mackay, E. G.; Raycroft, M. A. R.; Elfert, J.; Pratt, D. A.; Studer, A. J. Am. Chem. Soc. 2020, 142, 2609. doi: 10.1021/jacs.9b12343
[48]	Sekino, T.; Sato, S.; Yoshino, T.; Kojima, M.; Matsunaga, S. Org. Lett. 2022, 24, 2120. doi: 10.1021/acs.orglett.2c00319
[49]	(a) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Rev. 2016, 45, 2044.
	(b) Douglas, J. J.; Sevrin, M. J.; Stephenson, C. R. J. Org. Process Res. Dev. 2016, 20, 1134. doi: 10.1021/acs.oprd.6b00125
	(c) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. doi: 10.1021/acs.chemrev.6b00057
[50]	Sun, X.; Chen, J.; Ritter, T. Nat. Chem. 2018, 10, 1229. doi: 10.1038/s41557-018-0142-4
[51]	Cartwright, K. C.; Tunge, J. A. ACS Catal. 2018, 8, 11801. doi: 10.1021/acscatal.8b03282
[52]	Cartwright, K. C.; Joseph, E.; Comadoll, C. G.; Tunge, J. A. Chem. Eur. J. 2020, 26, 12454. doi: 10.1002/chem.202001952
[53]	Tlahuext-Aca, A.; Candish, L.; Garza-Sanchez, R. A.; Glorius, F. ACS Catal. 2018, 8, 1715. doi: 10.1021/acscatal.7b04281
[54]	Nguyen, V. T.; Nguyen, V. D.; Haug, G. C.; Dang, H. T.; Jin, S.; Li, Z.; Flores-Hansen, C.; Benavides, B. S.; Arman, H. D.; Larionov, O. V. ACS Catal. 2019, 9, 9485. doi: 10.1021/acscatal.9b02951
[55]	Tu, J.; Gao, H.; Luo, M.; Zhao, L.; Yang, C.; Guo, L.; Xia, W. Green Chem. 2022, 24, 5553. doi: 10.1039/D2GC01738E
[56]	Kumar, A.; Bhatti, T. M.; Goldman, A. S. Chem. Rev. 2017, 117, 12357. doi: 10.1021/acs.chemrev.7b00247
[57]	West, J. G.; Huang, D.; Sorensen, E. J. Nat. Commun. 2015, 6, 10093. doi: 10.1038/ncomms10093
[58]	Zhao, H.; McMillan, A. J.; Constantin, T.; Mykura, R. C.; Juliá, F.; Leonori, D. J. Am. Chem. Soc. 2021, 143, 14806. doi: 10.1021/jacs.1c06768
[59]	Zhou, M.-J.; Zhang, L.; Liu, G.; Xu, C.; Huang, Z. J. Am. Chem. Soc. 2021, 143, 16470. doi: 10.1021/jacs.1c05479
[60]	Parasram, M.; Chuentragool, P.; Wang, Y.; Shi, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2017, 139, 14857. doi: 10.1021/jacs.7b08459 pmid: 28992686
[61]	Parasram, M.; Chuentragool, P.; Sarkar, D.; Gevorgyan, V. J. Am. Chem. Soc. 2016, 138, 6340. doi: 10.1021/jacs.6b01628 pmid: 27149524
[62]	Chuentragool, P.; Parasram, M.; Shi, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2018, 140, 2465. doi: 10.1021/jacs.8b00488 pmid: 29400959
[63]	Jin, W.; Yu, S. Org. Lett. 2021, 23, 6931. doi: 10.1021/acs.orglett.1c02509
[64]	Yu, W.-L.; Ren, Z.-G.; Ma, K.-X.; Yang, H.-Q.; Yang, J.-J.; HaZheng, H.; Wu, W.; Xu, P.-F. Chem. Sci. 2022, 13, 7947. doi: 10.1039/D2SC02291E
[65]	Wang, C.-Y.; Azofra, L. M.; Dam, P.; Sebek, M.; Steinfeldt, N.; Rabeah, J.; El-Sepelgy, O. ACS Catal. 2022, 12, 8868. doi: 10.1021/acscatal.2c01723
[66]	Wang, X.; Li, Y.; Wu, X. ACS Catal. 2022, 12, 3710. doi: 10.1021/acscatal.2c00204
[67]	Grundmann, C. Justus Liebigs Ann. Chem. 1938, 536, 29. doi: 10.1002/jlac.19385360103
[68]	Xiao, T.; Mei, M.; He, Y.; Zhou, L. Chem. Commun. 2018, 54, 8865. doi: 10.1039/C8CC04609C
[69]	Wang, S.; Lokesh, N.; Hioe, J.; Gschwind, R. M.; König, B. Chem. Sci. 2019, 10, 4580. doi: 10.1039/C9SC00711C
[70]	(a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b pmid: 25255204
	(b) Klumpp, D. A. Synlett 2012, 23, 1590. doi: 10.1055/s-0031-1290984 pmid: 25255204
[71]	(a) Vorbrüggen, H.; Krolikiewcz, K. Tetrahedron Lett. 1983, 24, 889. doi: 10.1016/S0040-4039(00)81556-7
	(b) Zhang, G.; Irrgang, T.; Dietel, T.; Kallmeier, F.; Kempe, R. Angew. Chem. Int. Ed. 2018, 57, 9131. doi: 10.1002/anie.201801573
	(c) Kanyiva, K. S.; Nakao, Y.; Hiyama, T. Angew. Chem. Int. Ed. 2007, 46, 8872. doi: 10.1002/anie.200703758
[72]	Zhu, S.; Qin, J.; Wang, F.; Li, H.; Chu, L. Nat. Commun. 2019, 10, 749. doi: 10.1038/s41467-019-08669-1
[73]	(a) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. doi: 10.1021/cr960411r pmid: 18072810
	(b) McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841. doi: 10.1021/cr068402y pmid: 18072810
	(c) Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278. doi: 10.1021/ar200338s pmid: 18072810
[74]	Ye, C.; Cai, B.-G.; Lu, J.; Cheng, X.; Li, L.; Pan, Z.-W.; Xuan, J. J. Org. Chem. 2021, 86, 1012. doi: 10.1021/acs.joc.0c02500
[75]	Gao, P.-P.; Yan, D.-M.; Bi, M.-H.; Jiang, M.; Xiao, W.-J.; Chen, J.-R. Chem.-Eur. J. 2021, 27, 14195. doi: 10.1002/chem.202102671
[76]	Tian, X.; Karl, T. A.; Reiter, S.; Yakubov, S.; de Vivie-Riedle, R.; König, B.; Barham, J. P. Angew. Chem., Int. Ed. 2021, 60, 20817. doi: 10.1002/anie.202105895
[77]	(a) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898. doi: 10.1021/acs.joc.6b01449 pmid: 32490493
	(b) Marzo, L.; Pagire; Reiser, S. K. O.; König, B. Angew. Chem., Int. Ed. 2018, 57, 10034. doi: 10.1002/anie.201709766 pmid: 32490493
	(c) Holmberg-Douglas, N.; Nicewicz, D. A. Chem. Rev. 2022, 122, 1925. doi: 10.1021/acs.chemrev.1c00311 pmid: 32490493
	(d) Chen, H.; Yu, S.-Y. Org. Biomol. Chem. 2020, 18, 4519. doi: 10.1039/d0ob00854k pmid: 32490493