质子耦合电子转移在有机合成中的应用

doi:10.6023/cjoc202106001

摘要/Abstract

质子耦合电子转移(PCET)是一类非传统的氧化还原反应, 因其电子和质子转移过程具有独特的相互依赖性, 这类反应表现出特殊的反应性和选择性. PCET反应在包括天然和人工系统的氧化还原过程中, 如小分子活化等, 起到了相当关键的作用. 最近, PCET反应在有机合成中的应用引起了广泛的关注和兴趣. 人们实现了通过PCET机理的X—H键(如C—H键、N—H键、S—H键和O—H键等)的活化, 基于该过程合成了多种重要结构和基础骨架、获得了不同的合成砌块和天然产物. 此外, 通过PCET反应机理, 人们不仅获得了C=Y键等多重键的还原产物, 而且获得了底物之间的偶联产物. 综述了近年来PCET在有机合成中的应用和发展, 并且对该领域未来的发展进行了展望.

关键词: 质子耦合电子转移, 有机合成, 自由基反应, 官能化

Proton-coupled electron transfer (PCET) reactions are a kind of unconventional redox reactions, which exhibit special reactivities and selectivities due to their unique interdependent electron-proton transfer mechanisms. There are three possible pathways of PCET processes, including stepwise electron transfer followed by proton transfer (ETPT), proton transfer followed by electron transfer (PTET), and concerted pathway in which electron and proton transfer synchronously (CEPT), avoiding intermediates with high energy. These reactions have been playing a key role in numerous areas in organic chemistry, inorganic chemistry, bioorganic chemistry, organometallic and material chemistry, including the redox processes in natural and artificial systems, such as the activation for small molecules. Recently, the application of PCET reactions in organic synthesis has received a great deal of attentions and interests. Being accompanied by the development of electrochemical methods and photocatalysts, more and more novel reactions in electrochemistry and photochemistry involve PCET processes have been reported. Applying these electrochemical and photochemical methods, the activation of X—H bond has been achieved via PCET processes, including C—H bond, N—H bond, P—H bond, S—H bond or O—H bond. Thus, based on these crucial processes, a number of vital structures and fundamental frameworks can be synthesized, and various synthetic building blocks and natural products have been attained. For example, pharmaceutical building blocks like 2°-piperidines can be cyanated at their α-position; substituted dimeric pyrroloindolines such as (–)-calycanthidine, (–)-chimonanthine, and (–)-psychotriasine have also been successfully synthesized via PCET mechanism. Moreover, not only the products of reduction of multiple bonds (C=Y bond such as C=C bond, C=N bond and C=O bond), but also the products of self/cross-coupling have been achieved via PCET mechanism. In this review, the recent applications and developments of PCET mechanism in organic synthesis are summarized, including new catalyst systems and new reagents, especially with electrochemical and photochemical methodologies. The future of this area has also been demonstrated from both experimental and theoretical aspects.

Key words: proton-coupled electron transfer, organic synthesis, radical reactions, functionalization

引用此文

周子杰, 孔祥梅, 刘天飞. 质子耦合电子转移在有机合成中的应用[J]. 有机化学, 2021, 41(10): 3844-3879.

Zijie Zhou, Xiangmei Kong, Tianfei Liu. Applications of Proton-Coupled Electron Transfer in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3844-3879.

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图/表 80

Figure 1. Synthetic application of PCET

Figure 2. Concise illustration of HAT process with its BDFE equation (left), and illustrations of PCET processes with the corresponding effective BDFE equation (right)[38-39]

Scheme 1. Reactions via HAT and two types of PCET mechanism[34,40-41]

Figure 3. Three pathways of PCET mechanism (left)[6,13-14,45-46] and their corresponding reaction coordinates (right, redrawn from Acc Chem Res. 2016, 49(8), 1546~1556.)[7]

Scheme 2. C—H oxidation via MS-PCET mechanism

Scheme 3. Homo-dimerization of 3-aryl oxindoles via PCET pathways

Scheme 4. Asymmetric α-aryloxylation of cyclic ketones in the presence of quinones

Scheme 5. Intermolecular C—H alkylation of unactivated aliphatic C(sp3)—H bond

Scheme 6. C-alkylation of amines with alkyl bromides

Scheme 7. Cross-dehydrogenative coupling of C(sp3)—H and C(sp2)—H bonds

Scheme 8. Electrochemical α-cyanation of second piperidines and synthesis of amino acids

Scheme 9. Mn-mediated electrochemical synthesis of azaheterocycles

Scheme 10. Dimerization of 3-substituted 2-oxindoles

Scheme 11. Synthesis of 1-naphthols from alkynes and 1,3-dicarbonyl compounds

Scheme 12. Synthesis of benzylic alcohols by selective monooxidation of alkylated benzenes

Scheme 13. Visible-light-induced reductive Minisci reaction

Scheme 14. Electrochemical multicomponent synthesis of 4-selanylpyrazoles

Scheme 15. N—H activation in N-arylamides via a dual catalyst system

Scheme 16. N—H activation in N-arylamides a ternary catalyst system

Scheme 17. Catalytic N—H bond-weakening protocol for conjugate amination

Scheme 18. Catalytic alkylation of remote C—H bond

Scheme 19. Photocatalytic method to achieve alkoxyamine- substituted pyrroloindolines

Scheme 20. Intermolecular anti-Markovnikov hydroamination of unactivated alkenes

Scheme 21. Catalytic strategy for olefin hydroamidation with N-alkyl amides

Scheme 22. Intramolecular hydroamination of alkenes with sulfonamides

Scheme 23. Conjugate addition of nitrogen-based nucleophiles

Scheme 24. Stereoselective alkylation of C(sp3)—H bond

Scheme 25. Synthesis of alkyne- and alkene-decorated γ-lactams

Scheme 26. Synthesis of phenanthridinone and quinolinone derivatives

Scheme 27. Amidoarylation of unactivated olefin

Scheme 28. Construction of heteroarylamine via radical-radical cross-coupling pathway

Scheme 29. Anilide oxidation promoted by electrocatalytic way

Scheme 30. Electrochemical intramolecular oxidative amination reaction of tri- and tetra-substituted alkenes

Scheme 31. Electrochemical oxidative intramolecular C(sp3)—H amination of amides

Scheme 32. Oxidative homo-coupling of benzophenone imine

Scheme 33. Metal- and catalyst-free electrochemical synthesis of annulated medium-sized lactams

Scheme 34. Copper/TMEPO catalyzed aerobic oxidation reactions of alcohols

Scheme 35. Scalable, continuous-flow aerobic oxidation of primary alcohols

Scheme 36. Chemoselective metal-free aerobic oxidation for secondary benzylic alcohol in lignin

Scheme 37. Improved copper/nitroxyl catalyst system for the oxidation of functionalized primary and secondary alcohols

Scheme 38. Electrochemical oxidation of alcohols and aldehydes catalyzed by TEMPO•

Scheme 39. Oxidation of primary alcohols in lignin via electrochemical aminoxyl-mediated pathway

Scheme 40. Ring-cleavage and oxidative method for the isomerization of cyclic aliphatic alcohols

Scheme 41. Modular ring expansion of cyclic aliphatic alcohols

Scheme 42. Catalytic and light-driven method for the redox- neutral depolymerization of native lignin

Scheme 43. Remote arylation of ketones via photoredox-mediated multisite PCET

Scheme 44. Catalytic and light-driven method for the intramolecular hydroetherification of unactivated alkenols

Scheme 45. Synthesis of Z-alkenylphosphine oxides via visible-light-induced radical addition

Scheme 46. Visible-light-induced PCET strategy for the generation of phosphorus-centered radicals

Scheme 47. PCET reactions between a photoexcited Ru(II) complex and thiophenols

Scheme 48. C—H functionalization of benzyl ethers

Scheme 49. Synthesis of β-amino ether from C—H functionalization of ethers with imines

Scheme 50. Photocatalyst conjugation of thiols and alkenes

Scheme 51. Cascade coupling/cyclization reactions of aromatic amines

Scheme 52. Asymmetric aerobic decarboxylative Povarov reactions

Scheme 53. [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides

Scheme 54. Difunctionalization of alkenes in the presence of N-aryl α-amino acids

Scheme 55. Synthesis of chiral 3-aminomethylene-3-substituted oxindoles with quaternary carbon stereocenters

Scheme 56. Chemoselective reduction of α,β-unsaturated ketones to saturated ketones

Scheme 57. Enantioselective protonation triggered by the reductive cross coupling of olefin substrates

Scheme 58. Electrochemical hydrogenation of activated olefins

Scheme 59. Hydrogenation via electrochemical Birch reduction

Scheme 60. Chemoselective hydrogenation of unsaturated C—C bond

Scheme 61. Electrochemical reductive hydrogenation of α,β-unsaturated carbonyl compounds

Scheme 62. Synthesis of 1,3-diamines with a visible-light-mediated photocatalytic and umpolung method

Scheme 63. Synthesis of primary α-tertiary amines in quinone mediator

Scheme 64. Synthesis of primary hindered amines with fully substituted α-carbons by utilizing photoredox catalysis

Scheme 65. Synthesis of both hindered primary and secondary amines

Scheme 66. Synthesis of lactones by ketyl-olefin coupling

Scheme 67. Synthesis for cis-amino alcohols via concerted PCET

Scheme 68. Arylation for carbonyl/iminyl derivatives enabled by visible-light-mediated cross-coupling methods

Scheme 69. Formation of γ-functionalized vinylpyridines by catalytic addition of prochiral radicals

Scheme 70. Two plausible mechanisms for the formation of γ-functionalized vinylpyridines

Scheme 71. Electrochemical 1,4-hydrogenation of α,β-unsatu- rated ketones

Scheme 72. Cobalt-catalyzed ortho-specific regioselective nitration of aromatic C(sp2)—H bond

Scheme 73. Cu(I)-catalyzed enantioselective phosphinocyanation of styrenes

Scheme 74. Proposed mechanism for the cerium-catalyzed C—H functionalization

Figure 4. (A) A representative work of ES-PCET;[151] (B) ES-PCET in the research of the Marcus inverted region;[166] (C) electronic ground- and excited-state square schemes of PCET (redrawn from J. Am. Chem. Soc. 2021, 143, 560.[6])

Scheme 75. Coupling reactions with hydrogen evolution

Scheme 76. Proposed mechanism of coupling reactions with hydrogen evolution which may involve ES-PCET

参考文献 180

[1]	Hammes-Schiffer, S.; Iordanova, N. Biochim. Biophys. Acta 2004, 1655, 29. pmid: 15100013
[2]	Hammes-Schiffer, S. Acc. Chem. Res. 2009, 42, 1881. doi: 10.1021/ar9001284
[3]	Mayer, J. M. Annu. Rev. Phys. Chem. 2004, 55, 363. doi: 10.1146/annurev.physchem.55.091602.094446
[4]	Mayer, J. M.; Rhile, I. J. Biochim. Biophys. Acta 2004, 1655, 51.
[5]	Rhile, I. J.; Markle, T. F.; Nagao, H.; DiPasquale, A. G.; Lam, O. P.; Lockwood, M. A.; Rotter, K.; Mayer, J. M. J. Am. Chem. Soc. 2006, 128, 6075. pmid: 16669677
[6]	Tyburski, R.; Liu, T.; Glover, S. D.; Hammarström, L. J. Am. Chem. Soc. 2021, 143, 560. doi: 10.1021/jacs.0c09106 pmid: 33405896
[7]	Gentry, E. C.; Knowles, R. R. Acc. Chem. Res. 2016, 49, 1546. doi: 10.1021/acs.accounts.6b00272
[8]	Yang, J.-D.; Ji, P.; Xue, X.-S.; Cheng, J.-P. J. Am. Chem. Soc. 2018, 140, 8611. doi: 10.1021/jacs.8b04104
[9]	Wu, X.; Zhu, C. Chin. J. Chem. 2019, 37, 171.
[10]	Symes, M. D.; Surendranath, Y.; Lutterman, D. A.; Nocera, D. G. J. Am. Chem. Soc. 2011, 133, 5174. doi: 10.1021/ja110908v pmid: 21413703
[11]	Guo, Y.; Liu, Y.; Qi, J.; Li, H.; He, L.; Lu, L.; Liu, C.; Gong, L.; Zhao, D.; Yang, Z. Acta Chim. Sinica 2017, 75, 914. (in Chinese) doi: 10.6023/A17050214
	(郭宇, 刘瑜, 戚娟娟, 李慧, 赫兰兰, 卢丽男, 刘翠, 宫利东, 赵东霞, 杨忠志, 化学学报, 2017, 75, 914.) doi: 10.6023/A17050214
[12]	Odella, E.; Mora, S. J.; Wadsworth, B. L.; Huynh, M. T.; Goings, J. J.; Liddell, P. A.; Groy, T. L.; Gervaldo, M.; Sereno, L. E.; Gust, D.; Moore, T. A.; Moore, G. F.; Hammes-Schiffer, S.; Moore, A. L. J. Am. Chem. Soc. 2018, 140, 15450. doi: 10.1021/jacs.8b09724
[13]	Liu, T.; Guo, M.; Orthaber, A.; Lomoth, R.; Lundberg, M.; Ott, S.; Hammarström, L. Nat. Chem. 2018, 10, 881. doi: 10.1038/s41557-018-0076-x
[14]	Liu, T.; Tyburski, R.; Wang, S.; Fernandez-Teran, R.; Ott, S.; Hammarström, L. J. Am. Chem. Soc. 2019, 141, 17245. doi: 10.1021/jacs.9b08189
[15]	Bourrez, M.; Steinmetz, R.; Ott, S.; Gloaguen, F.; Hammarström, L. Nat. Chem. 2015, 7, 140. doi: 10.1038/nchem.2157
[16]	Jackson, M. N.; Pegis, M. L.; Surendranath, Y. ACS Cent. Sci. 2019, 5, 831. doi: 10.1021/acscentsci.9b00114
[17]	Wenger, O. S. Chem.-Eur. J. 2011, 17, 11692. doi: 10.1002/chem.v17.42
[18]	Wenger, O. S. Acc. Chem. Res. 2013, 46, 1517. doi: 10.1021/ar300289x
[19]	Chen, Z.; Wang, T.; Sun, T.; Chen, Z.; Sheng, T.; Hong, Y.-H.; Nan, Z.-A.; Zhu, J.; Zhou, Z.-Y.; Xia, H.; Sun, S.-G. Chin. J. Chem. 2018, 36, 1161. doi: 10.1002/cjoc.v36.12
[20]	Binstead, R. A.; Moyer, B. A.; Samuels, G. J.; Meyer, T. J. J. Am. Chem. Soc. 1981, 103, 2897. doi: 10.1021/ja00400a083
[21]	Liu, F.; Concepcion, J. J.; Jurss, J. W.; Cardolaccia, T.; Templeton, J. L.; Meyer, T. J. Inorg. Chem. 2008, 47, 1727. doi: 10.1021/ic701249s
[22]	Bonin, J.; Robert, M. Photochem. Photobiol. 2011, 87, 1190. doi: 10.1111/php.2011.87.issue-6
[23]	Hoffmann, N. Eur. J. Org. Chem. 2017, 2017, 1982. doi: 10.1002/ejoc.201601445
[24]	Hammes-Schiffer, S.; Soudackov, A. V. J. Phys. Chem. B 2008, 112, 14108. doi: 10.1021/jp805876e
[25]	Sanderson, R. T. Polar Covalence, Academic Press, New York, 1983, p. 46.
[26]	Sanderson, R. T. Chemical Bonds and Bond Energy, Academic Press, New York, 1976, p. 185.
[27]	Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
[28]	Bolton, J. R.; Archer, M. D. In Electron Transfer in Inorganic, Organic, and Biological Systems, American Chemical Society, Washington, 1991, pp. 7-23.
[29]	Marcus, R. A. J. Chem. Phys. 1956, 24, 966. doi: 10.1063/1.1742723
[30]	Borgis, D.; Hynes, J. T. J. Phy. Chem. 1996, 100, 1118. doi: 10.1021/jp9522324
[31]	Krishtalik, L. I. Biochim. Biophys. Acta 2000, 1458, 6. pmid: 10812022
[32]	Soudackov, A.; Hammes-Schiffer, S. J. Chem. Phys. 1999, 111, 4672. doi: 10.1063/1.479229
[33]	Soudackov, A.; Hammes-Schiffer, S. J. Chem. Phys. 2000, 113, 2385. doi: 10.1063/1.482053
[34]	Hammes-Schiffer, S.; Stuchebrukhov, A. A. Chem. Rev. 2010, 110, 6939. doi: 10.1021/cr1001436 pmid: 21049940
[35]	Huynh, M. H. V.; Meyer, T. J. Chem. Rev. 2007, 107, 5004. pmid: 17999556
[36]	Warren, J. J.; Tronic, T. A.; Mayer, J. M. Chem. Rev. 2010, 110, 6961. doi: 10.1021/cr100085k
[37]	Weinberg, D. R.; Gagliardi, C. J.; Hull, J. F.; Murphy, C. F.; Kent, C. A.; Westlake, B. C.; Paul, A.; Ess, D. H.; McCafferty, D. G.; Meyer, T. J. Chem. Rev. 2012, 112, 4016. doi: 10.1021/cr200177j pmid: 22702235
[38]	Waidmann, C. R.; Miller, A. J. M.; Ng, C.-W. A.; Scheuermann, M. L.; Porter, T. R.; Tronic, T. A.; Mayer, J. M. Energy Environ. Sci. 2012, 5, 7771. doi: 10.1039/c2ee03300c
[39]	Darcy, J. W.; Koronkiewicz, B.; Parada, G. A.; Mayer, J. M. Acc. Chem. Res. 2018, 51, 2391. doi: 10.1021/acs.accounts.8b00319
[40]	Morton, C. M.; Zhu, Q.; Ripberger, H.; Troian-Gautier, L.; Toa, Z. S. D.; Knowles, R. R.; Alexanian, E. J. J. Am. Chem. Soc. 2019, 141, 13253. doi: 10.1021/jacs.9b06834 pmid: 31356059
[41]	Tarantino, K. T.; Liu, P.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 10022. doi: 10.1021/ja404342j pmid: 23796403
[42]	Skone, J. H.; Soudackov, A. V.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2006, 128, 16655. doi: 10.1021/ja0656548
[43]	Liu, T.; Tyburski, R.; Wang, S.; Fernández-Terán, R.; Ott, S.; Hammarström, L. J. Am. Chem. Soc. 2019, 141, 17245. doi: 10.1021/jacs.9b08189
[44]	Huang, T.; Rountree, E. S.; Traywick, A. P.; Bayoumi, M.; Dempsey, J. L. J. Am. Chem. Soc. 2018, 140, 14655. doi: 10.1021/jacs.8b07102 pmid: 30362720
[45]	Darcy, J. W.; Kolmar, S. S.; Mayer, J. M. J. Am. Chem. Soc. 2019, 141, 10777. doi: 10.1021/jacs.9b04303
[46]	Zhang, J.; Yang, J.-D.; Cheng, J.-P. Chem. Sci. 2020, 11, 3672. doi: 10.1039/C9SC05883D
[47]	Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094. doi: 10.1002/anie.v48:28
[48]	Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J. Q. Chem. Soc. Rev. 2009, 38, 3242. doi: 10.1039/b816707a
[49]	Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788. doi: 10.1021/ar200185g
[50]	Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293. doi: 10.1021/cr100198w
[51]	Markle, T. F.; Darcy, J. W.; Mayer, J. M. Sci. Adv. 2018, 4, eaat5776. doi: 10.1126/sciadv.aat5776
[52]	Sayfutyarova, E. R.; Goldsmith, Z. K.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2018, 140, 15641. doi: 10.1021/jacs.8b10461 pmid: 30383371
[53]	Sayfutyarova, E. R.; Lam, Y. C.; Hammes-Schiffer, S. J. Am. Chem. Soc. 2019, 141, 15183. doi: 10.1021/jacs.9b06849 pmid: 31464122
[54]	Uraguchi, D.; Torii, M.; Ooi, T. ACS Catal. 2017, 7, 2765. doi: 10.1021/acscatal.7b00265
[55]	Shevchenko, G. A.; Oppelaar, B.; List, B. Angew. Chem., Int. Ed. 2018, 57, 10756. doi: 10.1002/anie.v57.33
[56]	Leng, L.; Ready, J. M. ACS Catal. 2020, 10, 13196. doi: 10.1021/acscatal.0c04519
[57]	Wu, Z. J.; Xu, H. C. Angew. Chem., Int. Ed. 2017, 56, 4734. doi: 10.1002/anie.201701329
[58]	Lennox, A. J. J.; Goes, S. L.; Webster, M. P.; Koolman, H. F.; Djuric, S. W.; Stahl, S. S. J. Am. Chem. Soc. 2018, 140, 11227. doi: 10.1021/jacs.8b08145
[59]	Zhang, Z.; Zhang, L.; Cao, Y.; Li, F.; Bai, G.; Liu, G.; Yang, Y.; Mo, F. Org. Lett. 2019, 21, 762. doi: 10.1021/acs.orglett.8b04010
[60]	Sharma, S.; Roy, A.; Shaw, K.; Bisai, A.; Paul, A. J. Org. Chem. 2020, 85, 14926. doi: 10.1021/acs.joc.0c01621
[61]	He, M. X.; Mo, Z. Y.; Wang, Z. Q.; Cheng, S. Y.; Xie, R. R.; Tang, H. T.; Pan, Y. M. Org. Lett. 2020, 22, 724. doi: 10.1021/acs.orglett.9b04549
[62]	Tanwar, L.; Borgel, J.; Ritter, T. J. Am. Chem. Soc. 2019, 141, 17983. doi: 10.1021/jacs.9b09496
[63]	Wang, Z.; Liu, Q.; Ji, X.; Deng, G.-J.; Huang, H. ACS Catal. 2019, 10, 154. doi: 10.1021/acscatal.9b04411
[64]	Wu, Y.; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950. doi: 10.1039/D1GC00562F
[65]	Peng, S.; Lin, Y.; He, W.-M. Chin. J. Org. Chem. 2020, 40, 541. (in Chinese) doi: 10.6023/cjoc202000006
	(彭莎, 林英武, 何卫民, 有机化学, 2020, 40, 541.) doi: 10.6023/cjoc202000006
[66]	Luo, Y. R. Handbook of Bond Dissociation Energies in Organic Compounds, CRC Press, Boca Raton, 2003.
[67]	Choi, G. J.; Knowles, R. R. J. Am. Chem. Soc. 2015, 137, 9226. doi: 10.1021/jacs.5b05377
[68]	Miller, D. C.; Choi, G. J.; Orbe, H. S.; Knowles, R. R. J. Am. Chem. Soc. 2015, 137, 13492. doi: 10.1021/jacs.5b09671 pmid: 26439818
[69]	Tarantino, K. T.; Miller, D. C.; Callon, T. A.; Knowles, R. R. J. Am. Chem. Soc. 2015, 137, 6440. doi: 10.1021/jacs.5b03428 pmid: 25945955
[70]	Choi, G. J.; Zhu, Q.; Miller, D. C.; Gu, C. J.; Knowles, R. R. Nature 2016, 539, 268. doi: 10.1038/nature19811
[71]	Gentry, E. C.; Rono, L. J.; Hale, M. E.; Matsuura, R.; Knowles, R. R. J. Am. Chem. Soc. 2018, 140, 3394. doi: 10.1021/jacs.7b13616 pmid: 29432006
[72]	Zhu, Q.; Graff, D. E.; Knowles, R. R. J. Am. Chem. Soc. 2018, 140, 741. doi: 10.1021/jacs.7b11144
[73]	Nguyen, S. T.; Zhu, Q.; Knowles, R. R. ACS Catal. 2019, 9, 4502. doi: 10.1021/acscatal.9b00966 pmid: 32292642
[74]	Roos, C. B.; Demaerel, J.; Graff, D. E.; Knowles, R. R. J. Am. Chem. Soc. 2020, 142, 5974. doi: 10.1021/jacs.0c01332
[75]	Zhou, Z.; Li, Y.; Han, B.; Gong, L.; Meggers, E. Chem. Sci. 2017, 8, 5757. doi: 10.1039/C7SC02031G
[76]	Yuan, W.; Zhou, Z.; Gong, L.; Meggers, E. Chem. Commun. 2017, 53, 8964. doi: 10.1039/C7CC04941B
[77]	Jia, J.; Ho, Y. A.; Bulow, R. F.; Rueping, M. Chem.-Eur. J. 2018, 24, 14054. doi: 10.1002/chem.v24.53
[78]	Moon, Y.; Jang, E.; Choi, S.; Hong, S. Org. Lett. 2018, 20, 240. doi: 10.1021/acs.orglett.7b03600
[79]	Zheng, S.; Gutierrez-Bonet, A.; Molander, G. A. Chem 2019, 5, 339. doi: 10.1016/j.chempr.2018.11.014
[80]	Zhou, C.; Lei, T.; Wei, X. Z.; Ye, C.; Liu, Z.; Chen, B.; Tung, C. H.; Wu, L. Z. J. Am. Chem. Soc. 2020, 142, 16805. doi: 10.1021/jacs.0c07600
[81]	Zhu, L.; Xiong, P.; Mao, Z. Y.; Wang, Y. H.; Yan, X.; Lu, X.; Xu, H. C. Angew. Chem., Int. Ed. 2016, 55, 2226. doi: 10.1002/anie.201510418
[82]	Xiong, P.; Xu, H. H.; Xu, H. C. J. Am. Chem. Soc. 2017, 139, 2956. doi: 10.1021/jacs.7b01016 pmid: 28199102
[83]	Hu, X.; Zhang, G.; Bu, F.; Nie, L.; Lei, A. ACS Catal. 2018, 8, 9370. doi: 10.1021/acscatal.8b02847
[84]	Wang, F.; Gerken, J. B.; Bates, D. M.; Kim, Y. J.; Stahl, S. S. J. Am. Chem. Soc. 2020, 142, 12349. doi: 10.1021/jacs.0c04626 pmid: 32520537
[85]	Xu, Z.; Huang, Z.; Li, Y.; Kuniyil, R.; Zhang, C.; Ackermann, L.; Ruan, Z. Green Chem. 2020, 22, 1099. doi: 10.1039/C9GC03901E
[86]	Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Acc. Chem. Res. 2005, 38, 851. doi: 10.1021/ar050113t
[87]	Uyanik, M.; Ishihara, K. Chem. Commun. 2009, 2086.
[88]	Ciriminna, R.; Pagliaro, M. Org. Process Res. Dev. 2010, 14, 245-251. doi: 10.1021/op900059x
[89]	Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901. doi: 10.1021/ja206230h
[90]	Greene, J. F.; Hoover, J. M.; Mannel, D. S.; Root, T. W.; Stahl, S. S. Org. Process Res. Dev. 2013, 17, 1247. doi: 10.1021/op400207f
[91]	Rahimi, A.; Azarpira, A.; Kim, H.; Ralph, J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 6415. doi: 10.1021/ja401793n
[92]	Steves, J. E.; Preger, Y.; Martinelli, J. R.; Welch, C. J.; Root, T. W.; Hawkins, J. M.; Stahl, S. S. Org. Process Res. Dev. 2015, 19, 1548. doi: 10.1021/acs.oprd.5b00179
[93]	Rafiee, M.; Konz, Z. M.; Graaf, M. D.; Koolman, H. F.; Stahl, S. S. ACS Catal. 2018, 8, 6738. doi: 10.1021/acscatal.8b01640
[94]	Rafiee, M.; Alherech, M.; Karlen, S. D.; Stahl, S. S. J. Am. Chem. Soc. 2019, 141, 15266. doi: 10.1021/jacs.9b07243
[95]	Ota, E.; Wang, H.; Frye, N. L.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, 1457. doi: 10.1021/jacs.8b12552
[96]	Zhao, K.; Yamashita, K.; Carpenter, J. E.; Sherwood, T. C.; Ewing, W. R.; Cheng, P. T. W.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, 8752. doi: 10.1021/jacs.9b03973 pmid: 31117664
[97]	Nguyen, S. T.; Murray, P. R. D.; Knowles, R. R. ACS Catal. 2019, 10, 800. doi: 10.1021/acscatal.9b04813
[98]	Huang, L.; Ji, T.; Rueping, M. J. Am. Chem. Soc. 2020, 142, 3532. doi: 10.1021/jacs.9b12490 pmid: 32017543
[99]	Tsui, E.; Metrano, A. J.; Tsuchiya, Y.; Knowles, R. R. Angew. Chem., Int. Ed. 2020, 59, 11845. doi: 10.1002/anie.v59.29
[100]	Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. doi: 10.1021/cr020049i
[101]	Piou, T.; Rovis, T. Nature 2015, 527, 86. doi: 10.1038/nature15691
[102]	Bayeh, L.; Le, P. Q.; Tambar, U. K. Nature 2017, 547, 196. doi: 10.1038/nature22805
[103]	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
[104]	Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079. doi: 10.1021/cr0201068
[105]	Xi, Y.; Dong, B.; McClain, E. J.; Wang, Q.; Gregg, T. L.; Akhmedov, N. G.; Petersen, J. L.; Shi, X. Angew. Chem., Int. Ed. 2014, 53, 4657. doi: 10.1002/anie.201310142
[106]	Hopkinson, M. N.; Tlahuext-Aca, A.; Glorius, F. Acc. Chem. Res. 2016, 49, 2261. doi: 10.1021/acs.accounts.6b00351
[107]	Patel, M.; Saunthwal, R. K.; Verma, A. K. Acc. Chem. Res. 2017, 50, 240. doi: 10.1021/acs.accounts.6b00449
[108]	Wang, J.; Zhang, S.; Xu, C.; Wojtas, L.; Akhmedov, N. G.; Chen, H.; Shi, X. Angew. Chem., Int. Ed. 2018, 57, 6915. doi: 10.1002/anie.v57.23
[109]	Wang, H.; Li, Y.; Tang, Z.; Wang, S.; Zhang, H.; Cong, H.; Lei, A. ACS Catal. 2018, 8, 10599. doi: 10.1021/acscatal.8b02617
[110]	Liu, Y.; Chen, X. L.; Li, X. Y.; Zhu, S. S.; Li, S. J.; Song, Y.; Qu, L. B.; Yu, B. J. Am. Chem. Soc. 2021, 143, 964. doi: 10.1021/jacs.0c11138
[111]	Kuss-Petermann, M.; Wenger, O. S. J. Phys. Chem. Lett. 2013, 4, 2535. doi: 10.1021/jz4012349
[112]	Griesbaum, K. Angew. Chem., Int. Ed. 1970, 9, 273. doi: 10.1002/(ISSN)1521-3773
[113]	Heiba, E.-A. I.; Dessau, R. M. J. Org. Chem. 1967, 32, 3837. doi: 10.1021/jo01287a025
[114]	Huyser, E. S.; Kellogg, R. M. J. Org. Chem. 1966, 31, 3366. doi: 10.1021/jo01348a059
[115]	Zhao, R.; Lind, J.; Merenyi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010. doi: 10.1021/ja00105a048
[116]	Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1999, 40, 8929. doi: 10.1016/S0040-4039(99)01898-5
[117]	Fujisawa, H.; Hayakawa, Y.; Sasaki, Y.; Mukaiyama, T. Chem. Lett. 2001, 30, 632. doi: 10.1246/cl.2001.632
[118]	Benati, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Scialpi, R.; Spagnolo, P.; Strazzari, S.; Zanardi, G. Angew. Chem., Int. Ed. 2004, 43, 3598. doi: 10.1002/(ISSN)1521-3773
[119]	Kemper, J.; Studer, A. Angew. Chem., Int. Ed. 2005, 44, 4914. doi: 10.1002/(ISSN)1521-3773
[120]	Dénès, F.; Pichowicz, M.; Povie, G.; Renaud, P. Chem. Rev. 2014, 114 2587. doi: 10.1021/cr400441m
[121]	Qvortrup, K.; Rankic, D. A.; MacMillan, D. W. J. Am. Chem. Soc. 2014, 136, 626. doi: 10.1021/ja411596q pmid: 24341523
[122]	Hager, D.; MacMillan, D. W. J. Am. Chem. Soc. 2014, 136, 16986. doi: 10.1021/ja5102695
[123]	Tyson, E. L.; Niemeyer, Z. L.; Yoon, T. P. J. Org. Chem. 2014, 79, 1427. doi: 10.1021/jo500031g
[124]	He, W.-B.; Gao, L.-Q.; Chen, X.-J.; Wu, Z.-L.; Huang, Y.; Cao, Z.; Xu, X.-H.; He, W.-M. Chin. Chem. Lett. 2020, 31, 1895. doi: 10.1016/j.cclet.2020.02.011
[125]	Li, J.; Gu, Z.; Zhao, X.; Qiao, B.; Jiang, Z. Chem. Commun. 2019, 55, 12916. doi: 10.1039/C9CC07380A
[126]	Liu, X.; Yin, Y.; Jiang, Z. Chem. Commun. 2019, 55, 11527. doi: 10.1039/C9CC06249A
[127]	Yang, H.; Wei, G.; Jiang, Z. ACS Catal. 2019, 9, 9599. doi: 10.1021/acscatal.9b03567
[128]	Zeng, G.; Li, Y.; Qiao, B.; Zhao, X.; Jiang, Z. Chem. Commun. 2019, 55, 11362. doi: 10.1039/C9CC05304B
[129]	Shi, J.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese) doi: 10.6023/cjoc202000041
	(时建伟, 魏伟, 有机化学, 2020, 40 2170.) doi: 10.6023/cjoc202000041
[130]	Prasanna, R.; Guha, S.; Sekar, G. Org. Lett. 2019, 21, 2650. doi: 10.1021/acs.orglett.9b00635
[131]	Kong, M.; Tan, Y.; Zhao, X.; Qiao, B.; Tan, C. H.; Cao, S.; Jiang, Z. J. Am. Chem. Soc. 2021, 143, 4024. doi: 10.1021/jacs.1c01073
[132]	Li, J.; He, L.; Liu, X.; Cheng, X.; Li, G. Angew. Chem., Int. Ed. 2019, 58, 1759. doi: 10.1002/anie.v58.6
[133]	Zimmerman, H. E. Acc. Chem. Res. 2012, 45, 164. doi: 10.1021/ar2000698
[134]	Benkeser, R. A.; Kaiser, E. M. J. Am. Chem. Soc. 1963, 85, 2858. doi: 10.1021/ja00901a047
[135]	Swenson, K. E.; Zemach, D.; Nanjundiah, C.; Kariv-Miller, E. J. Org. Chem. 1983, 48, 1777. doi: 10.1021/jo00158a042
[136]	Chaussard, J.; Combellas, C.; Thiebault, A. Tetrahedron Lett. 1987, 28, 1173.
[137]	Zhou, F.; Jehoulet, C.; Bard, A. J. J. Am. Chem. Soc. 1992, 114, 11004. doi: 10.1021/ja00053a072
[138]	Ishifune, M.; Yamashita, H.; Kera, Y.; Yamashita, N.; Hirata, K.; Murase, H.; Kashimura, S. Electrochim. Acta 2003, 48, 2405. doi: 10.1016/S0013-4686(03)00259-7
[139]	Peters, B. K.; Rodriguez, K. X.; Reisberg, S. H.; Beil, S. B.; Hickey, D. P.; Kawamata, Y.; Collins, M.; Starr, J.; Chen, L.; Udyavara, S.; Klunder, K.; Gorey, T. J.; Anderson, S. L.; Neurock, M.; Minteer, S. D.; Baran, P. S. Science 2019, 363, 838. doi: 10.1126/science.aav5606 pmid: 30792297
[140]	Qin, Y.; Lu, J.; Zou, Z.; Hong, H.; Li, Y.; Li, Y.; Chen, L.; Hu, J.; Huang, Y. Org. Chem. Front. 2020, 7, 1817. doi: 10.1039/D0QO00547A
[141]	Liu, X.; Liu, R.; Qiu, J.; Cheng, X.; Li, G. Angew. Chem., Int. Ed. 2020, 59, 13962. doi: 10.1002/anie.v59.33
[142]	Rossolini, T.; Leitch, J. A.; Grainger, R.; Dixon, D. J. Org. Lett. 2018, 20, 6794. doi: 10.1021/acs.orglett.8b02923 pmid: 30350662
[143]	Vasu, D.; Fuentes de Arriba, A. L.; Leitch, J. A.; de Gombert, A.; Dixon, D. J. Chem. Sci. 2019, 10, 3401. doi: 10.1039/C8SC05164J
[144]	Nicastri, M. C.; Lehnherr, D.; Lam, Y. H.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2020, 142, 987. doi: 10.1021/jacs.9b10871 pmid: 31904228
[145]	Lehnherr, D.; Lam, Y. H.; Nicastri, M. C.; Liu, J.; Newman, J. A.; Regalado, E. L.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2020, 142, 468. doi: 10.1021/jacs.9b10870 pmid: 31849221
[146]	Chen, M.; Zhao, X.; Yang, C.; Xia, W. Org. Lett. 2017, 19, 3807. doi: 10.1021/acs.orglett.7b01677
[147]	Cao, K.; Tan, S. M.; Lee, R.; Yang, S.; Jia, H.; Zhao, X.; Qiao, B.; Jiang, Z. J. Am. Chem. Soc. 2019, 141, 5437. doi: 10.1021/jacs.9b00286
[148]	Huang, B.; Li, Y.; Yang, C.; Xia, W. Chem. Commun. 2019, 55, 6731. doi: 10.1039/C9CC02368B
[149]	Nageswar Rao, D.; Rasheed, S.; Raina, G.; Ahmed, Q. N.; Jaladanki, C. K.; Bharatam, P. V.; Das, P. J. Org. Chem. 2017, 82, 7234. doi: 10.1021/acs.joc.7b00808
[150]	Zhang, G.; Fu, L.; Chen, P.; Zou, J.; Liu, G. Org. Lett. 2019, 21, 5015. doi: 10.1021/acs.orglett.9b01607
[151]	Li, H; Zhang, M. T. Angew. Chem., Int. Ed. 2016, 55, 13132. doi: 10.1002/anie.201607176
[152]	Schrauben, J. N.; Cattaneo, M.; Day, T. C.; Tenderholt, A. L.; Mayer, J. M. J. Am. Chem. Soc. 2012, 134, 16635. doi: 10.1021/ja305668h pmid: 22974135
[153]	Sirimanne, C. T.; Kerrigan, M. M.; Martin, P. D.; Kanjolia, R. K.; Elliott, S. D.; Winter, C. H. Inorg. Chem. 2015, 54, 7. doi: 10.1021/ic502184f pmid: 25488657
[154]	Canteenwala, T.; Padmawar, P. A.; Chiang, L. Y. J. Am. Chem. Soc. 2005, 127, 26. pmid: 15631431
[155]	Irebo, T.; Reece, S. Y.; Sjödin, M.; Nocera, D. G.; Hammarström, L. J. Am. Chem. Soc. 2007, 129, 15462. doi: 10.1021/ja073012u
[156]	Pizano, A. A.; Yang, J. L.; Nocera, D. G. Chem. Sci. 2012, 3, 2457. doi: 10.1039/c2sc20113e
[157]	Kuss-Petermann, M.; Wolf, H.; Stalke, D.; Wenger, O. S. J. Am. Chem. Soc. 2012, 134, 12844. doi: 10.1021/ja3053046 pmid: 22809316
[158]	Kuss-Petermann, M.; Wenger, O. S. J. Phys. Chem. A 2013, 117, 5726. doi: 10.1021/jp402567m pmid: 23834357
[159]	Chen, J.; Kuss-Petermann, M.; Wenger, O. S. Chem.-Eur. J. 2014, 20, 4098. doi: 10.1002/chem.201304256
[160]	Bronner, C.; Wenger, O. S. Phys. Chem. Chem. Phys. 2014, 16 3617.
[161]	Bowring, M. A.; Bradshaw, L. R.; Parada, G. A.; Pollock, T. P.; Fernández-Terán, R. J.; Kolmar, S. S.; Mercado, B. Q.; Schlenker, C. W.; Gamelin, D. R.; Mayer, J. M. J. Am. Chem. Soc. 2018, 140, 7449. doi: 10.1021/jacs.8b04455 pmid: 29847111
[162]	Sayfutyarova, E. R.; Hammes-Schiffer, S. J. Phys. Chem. Lett. 2020, 11, 7109. doi: 10.1021/acs.jpclett.0c02012 pmid: 32787327
[163]	Eisenhart, T. T.; Dempsey, J. L. J. Am. Chem. Soc. 2014, 136, 12221. doi: 10.1021/ja505755k pmid: 25046022
[164]	Swords, W. B.; Meyer, G. J.; Hammarström, L. Chem. Sci. 2020, 11, 3460. doi: 10.1039/C9SC04941J
[165]	Lennox, J. C.; Kurtz, D. A.; Huang, T.; Dempsey, J. L. ACS Energy Lett. 2017, 2, 1246. doi: 10.1021/acsenergylett.7b00063
[166]	Parada, G. A.; Goldsmith, Z. K.; Kolmar, S.; Pettersson Rimgard, B.; Mercado, B. Q.; Hammarström, L.; Hammes-Schiffer, S.; Mayer, J. M. Science 2019, 364, 471. doi: 10.1126/science.aaw4675
[167]	Guo, J. D.; Yang, X. L.; Chen, B.; Tung, C. H.; Wu, L. Z. Org. Lett. 2020, 22, 9627. doi: 10.1021/acs.orglett.0c03665
[168]	Lei, T.; Liang, G.; Cheng, Y. Y.; Chen, B.; Tung, C. H.; Wu, L. Z. Org. Lett. 2020, 22, 5385. doi: 10.1021/acs.orglett.0c01709
[169]	Wang, J. H.; Li, X. B.; Li, J.; Lei, T.; Wu, H. L.; Nan, X. L.; Tung, C. H.; Wu, L. Z. Chem. Commun. 2019, 55, 10376. doi: 10.1039/C9CC05375A
[170]	Wang, J. H.; Lei, T.; Nan, X. L.; Wu, H. L.; Li, X. B.; Chen, B.; Tung, C. H.; Wu, L. Z. Org. Lett. 2019, 21, 5581. doi: 10.1021/acs.orglett.9b01910
[171]	Huang, C.; Wang, J. H.; Qiao, J.; Fan, X. W.; Chen, B.; Tung, C. H.; Wu, L. Z. J. Org. Chem. 2019, 84, 12904. doi: 10.1021/acs.joc.9b01603
[172]	Li, H.; Guo, Y. H.; Wu, J. Y.; Zhang, M. T. Chem. Commun. 2019, 55, 3465. doi: 10.1039/C9CC00354A
[173]	Chen, J.; Chen, J.; Liu, Y.; Zheng, Y.; Zhu, Q.; Han, G.; Shen, J.-R. J. Phys. Chem. Lett. 2019, 10, 3240. doi: 10.1021/acs.jpclett.9b00959 pmid: 31117681
[174]	Ren, X.; Wang, X.; Sun, Y.; Chi, X.; Mangel, D.; Wang, H.; Sessler, J. L. Org. Chem. Front. 2019, 6, 584. doi: 10.1039/C8QO01408F
[175]	Lin, Y.; Yan, Y.; Peng, W.; Qiao, X.; Huang, D.; Ji, H.; Chen, C.; Ma, W.; Zhao, J. J. Phys. Chem. Lett. 2020, 11, 3941. doi: 10.1021/acs.jpclett.0c01196
[176]	Zhang, X.; Ma, J.; Li, S.; Li, M.-D.; Guan, X.; Lan, X.; Zhu, R.; Phillips, D. L. J. Org. Chem. 2016, 81, 5330. doi: 10.1021/acs.joc.6b00620
[177]	Xu, Y.; Bao, P.; Song, K.; Shi, Q. J. Comput. Chem. 2019, 40, 1005. doi: 10.1002/jcc.v40.9
[178]	Zhong, W.; Wu, L.; Jiang, W.; Li, Y.; Mookan, N.; Liu, X. Dalton Trans. 2019, 48, 13711. doi: 10.1039/c9dt02058f pmid: 31469134
[179]	Giret, Y.; Guo, P.; Wang, L.-F.; Cheng, J. J. Chem. Phys. 2020, 152, 124705. doi: 10.1063/5.0001825
[180]	Song, K.; Shi, Q. J. Chem. Phys. 2017, 146, 184108. doi: 10.1063/1.4982928