氮宾/炔烃复分解串联反应研究进展

doi:10.6023/cjoc202109035

摘要/Abstract

在过去的几十年中, 氮宾催化转化作为一类直接构建C—N键的高效反应得到了飞速发展, 并被广泛应用于含氮杂环化合物的合成. 虽然已有多种类型的氮宾前体被报道, 并通过各类催化转化反应在构建结构多样性杂环化合物分子中起到了至关重要的作用, 然而, 氮宾的反应类型还是局限于胺化反应、氮杂环丙烷化反应、磺化反应等有限的几类反应. 基于氮宾前体、催化策略(或者催化剂)以及复杂分子合成的相关综述已有很多报道, 这篇综述聚焦氮宾与炔烃的加成反应, 主要是氮宾/炔烃复分解串联反应. 这类反应可以快速合成具有结构多样性的多环、稠环和螺环类含氮杂环类化合物.

关键词: 氮宾, α-亚胺卡宾, 含氮杂环化合物, 氮宾/炔烃复分解, 串联反应

Catalytic nitrene transformations to N-containing molecules through direct C—N bond formation have experienced a dramatic development in the last decades. Although a variety of nitrene precursors have been disclosed under the corresponding catalytic conditions, which play a principal role in the synthesis of nitrogen-containing molecules with structural complexity, the types of nitrene transfer reactions mainly limited to the amination, aziridination, sulfimidation, and few others. In this area, reviews focused on different nitrene precursors, catalytic strategy (or metal catalysts), and challenging synthesis have been well-documented. In this review, the catalytic approaches of nitrene addition with alkynes, mainly nitrene/alkyne metathesis cascade reactions are outlined, which provide expeditious access to polycyclic, fused, and spiro N-heterocycles with structural diversity.

Key words: nitrene, α-imino carbene, N-heterocycle, nitrene/alkyne metathesis, cascade reaction

引用此文

洪科苗, 黄晶晶, 姚铭瀚, 徐新芳. 氮宾/炔烃复分解串联反应研究进展[J]. 有机化学, 2022, 42(2): 344-352.

Kemiao Hong, Jingjing Huang, Minghan Yao, Xinfang Xu. Recent Advances in Nitrene/Alkyne Metathesis Cascade Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 344-352.

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图/表 13

Figure 1. Publication and citation report of nitrene from Web of Science (1967~2021)

Scheme 1. Summary of nitrene precursors and catalysts/catalytic conditions

Scheme 2. Summary of catalytic nitrene transfer reactions

Scheme 3. Rh-catalyzed intramolecular cascade NAM reaction terminated by ylide rearrangement

Scheme 4. Rh-catalyzed intermolecular cascade NAM reaction terminated by ylide rearrangement

Scheme 5. Asymmetric cascade NAM reaction terminated by ylide arrangement

Scheme 6. Cascade NAM reaction terminated by a formal C—N bond insertion

Scheme 7. Cascade NAM reaction terminated by aromatic C—H functionalization or cyclopropanation

Scheme 8. Cascade NAM reaction terminated by Buchner reaction

Scheme 9. Cu-catalyzed cascade NAM reaction terminated by Buchner reaction or oxidation

Scheme 10. Cascade NAM reaction terminated by oxidation

Scheme 11. Cascade NAM reaction terminated by 1,2-alkyl migration

Scheme 12. Fe-catalyzed formal [3+2] annulation via metalloradical intermediate

参考文献 64

[1]	Tiemann, F. Ber. Dtsch. Chem. Ges. 1891, 24, 4162. doi: 10.1002/cber.v24:2
[2]	(a) Egger, J.; Carreira, E. M. Nat. Prod. Rep. 2014, 31, 449. doi: 10.1039/C3NP70084D
	(b) Darses, B.; Rodrigues, R.; Neuville, L.; Mazurais, M.; Dauban, P. Chem. Commun. 2017, 53, 493. doi: 10.1039/C6CC07925C
	(c) Hazelard, D.; Nocquet, P.-A.; Compain, P. Org. Chem. Front. 2017, 4, 2500. doi: 10.1039/C7QO00547D
	(d) Zhang, J.; Pérez-Temprano, M. H. Chimia 2020, 74, 895. doi: 10.2533/chimia.2020.895
[3]	(a) Smith, P. A. S.; Brown, B. B. J. Am. Chem. Soc. 1951, 73, 2435. doi: 10.1021/ja01150a008
	(b) Smith, P. A. S.; Clegg, J. M.; Hall, J. H. J. Org. Chem. 1958, 23, 524. doi: 10.1021/jo01098a006
[4]	(a) Lwowski, W.; Mattingly, T. W. Tetrahedron Lett. 1962, 3, 277. doi: 10.1016/S0040-4039(00)70866-5
	(b) Lwowski, W.; Mattingly, T. W. J. Am. Chem. Soc. 1965, 87, 1947. doi: 10.1021/ja01087a019
[5]	(a) Sloan, M. F.; Renfrow, W. B.; Breslow, D. S. Tetrahedron Lett. 1964, 5, 2905. doi: 10.1016/S0040-4039(00)70443-6
	(b) Breslow, D. S.; Sloan, M. F.; Newburg, N. R.; Renfrow, W. B. J. Am. Chem. Soc. 1969, 91, 2273. doi: 10.1021/ja01037a016
[6]	(a) Smolinsky, G. J. Am. Chem. Soc. 1960, 82, 4717. doi: 10.1021/ja01502a065
	(b) ApSimon, J. W.; Edwards, O. E. Can. J. Chem. 1962, 40, 896. doi: 10.1139/v62-136
	(c) Masamune, S. J. Am. Chem. Soc. 1964, 86, 290. doi: 10.1021/ja01056a042
	(d) Anastassiou, A. G.; Simmons, H. E.; Marsh, F. D. J. Am. Chem. Soc. 1965, 87, 2296. doi: 10.1021/ja01088a043
[7]	Kwart, H.; Khan, A. A. J. Am. Chem. Soc. 1967, 89, 1951. doi: 10.1021/ja00984a035
[8]	Ullman, E. F.; Singh, B. J. Am. Chem. Soc. 1966, 88, 1844. doi: 10.1021/ja00960a066
	(b) Nunes, C. M.; Reva, I.; Melo, T. M. V. D. P. E.; Fausto, R. J. Org. Chem. 2012, 77, 8723. doi: 10.1021/jo301699z
[9]	Sauer, J.; Mayer, K. K. Tetrahedron Lett. 1968, 9, 319. doi: 10.1016/S0040-4039(01)98753-2
[10]	Sauer, J.; Mayer, K. K. Tetrahedron Lett. 1968, 3, 325. doi: 10.1016/0040-4020(58)80037-X
[11]	Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett. 1975, 361.
[12]	(a) Breslow, R.; Gellman, S. H. J. Chem. Soc. Chem. Commun. 1982, 1400.
	(b) Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 105, 6728. doi: 10.1021/ja00360a039
[13]	Mansuy, D.; Mahy, J.-P.; Dureault, A.; Bedi, G.; Battioni, P. J. Chem. Soc., hem. Commun. 1984, 1161.
[14]	(a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328. doi: 10.1021/ja00065a068
	(b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742. doi: 10.1021/ja00086a007
[15]	Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326. doi: 10.1021/ja00065a067
[16]	Müller, P.; Baud, C.; Jacquier, Y. Tetrahedron 1996, 52, 1543. doi: 10.1016/0040-4020(95)00999-X
[17]	Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233. pmid: 10930251
[18]	Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935. doi: 10.1021/ja011033x
[19]	Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. J. Am. Chem. Soc. 2001, 123, 7707. pmid: 11480997
[20]	(a) Dequirez, G.; Pons, V.; Dauban, P. Angew. Chem., Int. Ed. 2012, 51, 7384. doi: 10.1002/anie.201201945 pmid: 32064858
	(b) Wentrup, C. Angew. Chem. Int. Ed. 2018, 57, 11508. doi: 10.1002/anie.v57.36 pmid: 32064858
	(c) Chu, J. C. K.; Rovis, T. Angew. Chem. Int. Ed. 2018, 57, 62. doi: 10.1002/anie.201703743 pmid: 32064858
	(d) Trowbridge, A.; Scarlett, S. M.; Gaunt, M. L. Chem. Rev. 2020, 120, 2613. doi: 10.1021/acs.chemrev.9b00462 pmid: 32064858
[21]	(a) Driver, T. G. Org. Biomol. Chem. 2010, 8, 3831. doi: 10.1039/c005219c pmid: 20617243
	(b) Intrieri, D.; Zardi, P.; Caselli, A.; Gallo, E. Chem. Commun. 2014, 50, 11440. doi: 10.1039/C4CC03016H pmid: 20617243
	(c) Shin, K.; Kim, H.; Chang, S. Acc. Chem. Res. 2015, 48, 1040. doi: 10.1021/acs.accounts.5b00020 pmid: 20617243
[22]	(a) Shimbayashi, T.; Sasakura, K.; Eguchi, A.; Okamoto, K.; Ohe, K. Chem. Eur. J. 2019, 25, 3156.
	(b) Van Vliet, K. M.; Bruin, B. ACS Catal. 2020, 10, 4751. doi: 10.1021/acscatal.0c00961
[23]	Green, M.; Mercer, R. J.; Morton, C. E.; Orpen, A. G. Angew. Chem. Int. Ed. Engl. 1985, 24, 422. doi: 10.1002/(ISSN)1521-3773
[24]	Okamoto, K.; Oda, T.; Kohigashi, S.; Ohe, K. Angew. Chem. Int. Ed. 2011, 50, 11470. doi: 10.1002/anie.v50.48
[25]	Das, S. K.; Roy, S.; Khatua, H.; Chattopadhyay, B. J. Am. Chem. Soc. 2018, 140, 8429. doi: 10.1021/jacs.8b05343
[26]	Wang, Y.-C.; Lai, X.-J.; Huang, K.; Yadav, S.; Qiu, G.; Zhang, L.; Zhou, H. Org. Chem. Front. 2021, 8, 1677. doi: 10.1039/D0QO01360A
[27]	(a) Mondal, R. R.; Khamarui, S.; Maiti, D. K. Org. Lett. 2017, 19, 5964. doi: 10.1021/acs.orglett.7b02844 pmid: 29056045
	(b) Deng, T. N.; Mazumdar, W.; Ford, R. L.; Jana, N.; Izar, R.; Wink, D. J.; Driver, T. G. J. Am. Chem. Soc. 2020, 142, 4456. doi: 10.1021/jacs.9b13599 pmid: 29056045
[28]	Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676. doi: 10.1021/ja100676r
[29]	Liu, G.; Zhang, Y.; Yuan, Y.; Xu, H. J. Am. Chem. Soc. 2013, 135, 3343. doi: 10.1021/ja311923z
[30]	(a) McIntosh, J. A.; Coelho, P. S.; Farwell, C. C.; Wang, Z. J.; Lewis, J. C.; Brown, T. R.; Arnold, F. A. Angew. Chem., Int. Ed. 2013, 52, 9309. doi: 10.1002/anie.201304401 pmid: 31611634
	(b) Mahy, J.-P.; Ciesielski, J.; Dauban, P. Angew. Chem., Int. Ed. 2014, 53, 6862. doi: 10.1002/anie.201403654 pmid: 31611634
	(c) Singh, R.; Bordeaux, M.; Fasan, R. ACS Catal. 2014, 4, 546. doi: 10.1021/cs400893n pmid: 31611634
	(d) Prier, C. K.; Zhang, R. K.; Buller, A. R.; Brinkmann-Chen, S.; Arnold, F. H. Nat. Chem. 2017, 9, 629. doi: 10.1038/nchem.2783 pmid: 31611634
	(e) Yang, Y.; Cho, I.; Qi, X.; Liu, P.; Arnold, F. A. Nat. Chem. 2019, 11, 987. doi: 10.1038/s41557-019-0343-5 pmid: 31611634
[31]	(a) Gephart, R. T.; III.; Warren, T. H. Organometallics 2012, 31, 7728. doi: 10.1021/om300840z
	(b) Rodríguez, M. R.; Díaz-Requejo, M. M.; Pérez, P. J. Synlett 2021, 32, 763. doi: 10.1055/s-0040-1706534
[32]	Nägeli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087. doi: 10.1002/hlca.v80:4
[33]	(a) Plietker, B.; Röske, A. Catal. Sci. Technol. 2019, 9, 4188. doi: 10.1039/c9cy00675c
	(b) Wang, P.; Deng, L. Chin. J. Chem. 2018, 36, 1222. doi: 10.1002/cjoc.v36.12
[34]	Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073. doi: 10.1021/ja00345a071
[35]	Cenini, S.; Tollari, S.; Penoni, A.; Cereda, C. J. Mol. Catal. A 1999, 137, 135. doi: 10.1016/S1381-1169(98)00116-2
[36]	For review: a Intrieri, D.; Carminati, D. M.; Gallo, E. J. Porphyrins Phthalocyanines 2016, 20, 190. doi: 10.1142/S1088424616500383
	Selected recent advance: doi: 10.1016/j.chempr.2020.07.005
	(b) Leest, N. P.; Vliet, K. M.; Bruin, B. Chem 2020, 6, 1851.
[37]	(a) Kuijpers, P. F.; Tiekink, M. J.; Breukelaar, W. B.; Broere, D. L. J.; Leest, N. P.; Vlugt, J. I.; Reek, J. N. H.; Bruin, B. Chem. Eur. J. 2017, 23, 7945. doi: 10.1002/chem.201700358
	(b) Li, C.-Q.; Lang, K.; Lu, H. J.; Hu, Y.; Cui, X.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2018, 57, 16837. doi: 10.1002/anie.v57.51
	(c) Hu, Y.; Lang, K.; Li, C.; Gill, J. B.; Kim, I.; Lu, H.; Fields, K. B.; Marshall, M.; Cheng, Q.; Cui, X.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2019, 141, 18160. doi: 10.1021/jacs.9b08894
[38]	For reviews: a Alderson, J. M.; Corbin, J. R.; Schomaker, J. M. Acc. Chem. Res. 2017, 50, 2147. doi: 10.1021/acs.accounts.7b00178 pmid: 32255621
	(b) Zhang, J.; Shan, C.; Zhang, T.; Song, J.; Liu, T.; Lan, Y. Coord. Chem. Rev. 2019, 382, 69. doi: 10.1016/j.ccr.2018.12.009 pmid: 32255621
	Pioneering work and selected examples: doi: 10.1021/ja038668b pmid: 32255621
	(c) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202. doi: 10.1021/ja412547r pmid: 32255621
	(d) Llaveria, J.; Beltrán, Á.; Sameera, W. M. C.; Locati, A.; DíazRequejo, M. M.; Matheu, M. I.; Castillón, S.; Maseras, F.; Pérez, P. J. J. Am. Chem. Soc. 2014, 136, 5342. doi: 10.1021/ja406654y pmid: 32255621
	(e) Rigoli, J. W.; Weatherly, C. D.; Alderson, J. M.; Vo, B. T.; Schomaker, J. M. J. Am. Chem. Soc. 2013, 135, 17238. doi: 10.1021/jacs.0c02803 pmid: 32255621
	(f) Annapureddy, R. R.; Jandl, C.; Bach, T. J. Am. Chem. Soc. 2020, 142, 7374. pmid: 32255621
[39]	Other metal catalysts: For Zn: a Breslow, D. S.; Sloan, M. F. Tetrahedron Lett. 1968, 5349. pmid: 21774482
	For, Pd: doi: 10.1246/bcsj.55.3943 pmid: 21774482
	(b) Migita, T.; Chiba, T.; Takahashi, K.; Siatoh, N.; Nkaido, S.; Kosugi, M. Bull. Chem. Soc. Jpn 1982, 55, 3943. doi: 10.1021/ja502164f pmid: 21774482
	(c) Broere, D. L. J.; Bruin, B.; Reek, J. N. H.; Lutz, M.; Dechert, S.; Vlugt, J. I. J. Am. Chem. Soc. 2014, 136, 11574. doi: 10.1021/ic200911b pmid: 21774482
	For Ta and Zr: pmid: 21774482
	(d) Heyduk, A. F.; Zarkesh, R. A.; Nguyen, A. I. Inorg. Chem. 2011, 50, 9849. pmid: 21774482
[40]	(a) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935. doi: 10.1021/ja011033x
	(b) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598. doi: 10.1002/1521-3773(20010202)40:3【-逻辑与-】#x00026;lt;【-逻辑与-】#x00026;gt;1.0.CO;2-A
	(c) Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911. doi: 10.1021/ar200318q
[41]	Thacker, N. C.; Lin, Z.; Zhang, T.; Gilhula, J. C.; Abney, C. W.; Lin, W. J. Am. Chem. Soc. 2016, 138, 3501. doi: 10.1021/jacs.5b13394 pmid: 26885768
[42]	Paradine, S. M.; Griffin, J. R.; Zhao, J.; Petronico, A. L.; Miller, S. M.; White, M. C. Nat. Chem. 2015, 7, 987. doi: 10.1038/nchem.2366 pmid: 26587714
[43]	Hong, S. Y.; Park, Y.; Hwang, Y.; Kim, Y. B.; Baik, M. H.; Chang, S. Science 2018, 359, 1016. doi: 10.1126/science.aap7503
[44]	(a) Hayashi, H.; Uchida, T. Eur. J. Org. Chem. 2020, 909.
	(b) Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247. doi: 10.1021/acs.chemrev.6b00644
	(c) Wang, P.; Deng, L. Chin. J. Chem. 2018, 36, 1222. doi: 10.1002/cjoc.v36.12
[45]	(a) Shen, M.; Leslie, B. E.; Driver, T. G. Angew. Chem. Int. Ed. 2008, 47, 5056. doi: 10.1002/anie.v47:27
	(b) Stokes, B. J.; Jovanovic, B.; Dong, H.; Richert, K. J.; Riell, R. D.; Driver, T. G. J. Org. Chem. 2009, 74, 3225. doi: 10.1021/jo9002536
[46]	Ton, T. M.; Tejo, C.; Tania, S.; Chang, J. W.; Chan, P. W. J. Org. Chem. 2011, 76, 4894. doi: 10.1021/jo200284a
[47]	(a) Uchida, T.; Katsuki, T. Chem. Rec. 2014, 14, 117. doi: 10.1002/tcr.v14.1 pmid: 12914485
	(b) Damiano, C.; Intrieri, D.; Gallo, E. Inorg. Chim. Acta 2018, 470, 51. doi: 10.1016/j.ica.2017.06.032 pmid: 12914485
	(c) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905. pmid: 12914485
	(d) Halfen, J. A. Curr. Org. Chem. 2005, 9, 657. doi: 10.2174/1385272053765024 pmid: 12914485
	(e) Changm, J. W. W.; Ton, T. M. U.; Chan, P. W. H. Chem. Rec. 2011, 11, 331. doi: 10.1002/tcr.201100018 pmid: 12914485
[48]	(a) Mancheño, O. G.; Bolm, C. Chem. Eur. J. 2007, 13, 6674. doi: 10.1002/(ISSN)1521-3765 pmid: 32357006
	(b) Yoshitake, M.; Hayashi, H.; Uchida, T. Org. Lett. 2020, 22, 4021. doi: 10.1021/acs.orglett.0c01373 pmid: 32357006
	(c) Lam, T. L.; Tso, K. C.-H.; Cao, B.; Yang, C.; Chen, D.; Chang, X. Y.; Huang, J. S.; Che, C. M. Inorg. Chem. 2017, 56, 4253. doi: 10.1021/acs.inorgchem.7b00226 pmid: 32357006
	(d) Wang, J.; Frings, M.; Bolm, C. Angew. Chem. Int. Ed. 2013, 125, 8823. doi: 10.1002/ange.201304451 pmid: 32357006
	(e) Xiao, X. S.; Huang, S. P.; Tang, S. S.; Jia, G. K.; Ou, G. C.; Li, Y. Y. J. Org. Chem. 2019, 84, 7618. doi: 10.1021/acs.joc.9b00281 pmid: 32357006
[49]	(a) Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Gotti, C. L.; Lapadula, M.; Mangioni, E.; Cenini, S. Chem. Eur. J. 2003, 9, 249. doi: 10.1002/chem.200390018 pmid: 22381423
	(b) Harrold, N. D.; Waterman, R.; Hillhouse, G. L.; Cundari, T. R. J. Am. Chem. Soc. 2009, 131, 12872. doi: 10.1021/ja904370h pmid: 22381423
	(c) Takaoka, A.; Moret, M.-E.; Peters, J. C. J. Am. Chem. Soc. 2012, 134, 6695. doi: 10.1021/ja211603f pmid: 22381423
[50]	Doyle, M. P. In Reactive Intermediate Chemistry, Chapter 12, Eds.: Moss, R. A.; Platz, M. S.; Jones, Jr., M., Wiley, New York, 2004, pp. 561-592.
[51]	For review: a Pei, C.; Zhang, C.; Qian, Y.; Xu, X. Org. Biomol. Chem. 2018, 16, 8677. doi: 10.1039/C8OB02420K
	Selected recent advances: doi: 10.1039/C7CC08221E
	(b) Zheng, Y.; Bao, M.; Yao, R.; Qiu, L.; Xu, X. Chem. Commun. 2018, 54, 350. doi: 10.1021/acscatal.8b04144
	(c) Zhang, C.; Li, H.; Pei, C.; Qiu, L.; Hu, W.; Bao, X.; Xu, X. ACS Catal. 2019, 9, 2440.
	(d) Dong, K.; Fan, X.; Pei, C.; Zheng, Y.; Chang, S.; Cai, J.; Qiu, L.; Yu, Z.; Xu, X. Nat. Common. 2020, 11, 2363. doi: 10.1038/s41467-021-21335-9
	(e) Zhang, C.; Hong, K.; Pei, C.; Zhou, S.; Hu, W.; Hashmi, A. S. K.; Xu, X. Nat. Commun. 2021, 12, 1182. doi: 10.1002/adsc.v363.16
	(f) Bao, M.; Xie, X.; Hu, W.; Xu, X. Adv. Syn. Cat. 2021, 363, 4018.
[52]	For reviews: a Davies, P. W.; Garzon, M. Asian J. Org. Chem. 2015, 4, 694. doi: 10.1002/ajoc.v4.8
	(b) Liao, Y.; Zhu, L.; Yu, Y.; Chen, G.; Huang, X. Chin. J. Org. Chem. 2017, 37, 2785. doi: 10.6023/cjoc201708021
	(c) Tian, X.; Song, L.; Hashmi, A. S. K. Chem. Eur. J. 2020, 26, 3197. doi: 10.1002/chem.v26.15
[53]	Early examples and selected advances: a Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260. doi: 10.1021/ja053804t pmid: 29652163
	(b) Li, C.; Zhang, L. Org. Lett. 2011, 13, 1738. doi: 10.1021/ol2002607 pmid: 29652163
	(c) Gronnier, C.; Boissonnat, G.; Gagosz, F. Org. Lett. 2013, 15, 4234. doi: 10.1021/ol4019634 pmid: 29652163
	(d) Matsuoka, J.; Matsuda, Y.; Kawada, Y.; Oishi, S.; Ohno, H. Angew. Chem., Int. Ed. 2017, 56, 7444. doi: 10.1002/anie.201703279 pmid: 29652163
	(e) Cai, J.; Wu, B.; Rong, G.; Zhang, C.; Qiu, L.; Xu, X. Org. Lett. 2018, 20, 2733. doi: 10.1021/acs.orglett.8b00939 pmid: 29652163
	(f) Saito, A.; Kambara, Y.; Yagyu, T.; Noguchi, K.; Yoshimura, A.; Zhdankin, V. V. Adv. Synth. Catal. 2015, 357, 667. doi: 10.1002/adsc.v357.4 pmid: 29652163
[54]	Thornton, A. R.; Blakey, S. B. J. Am. Chem. Soc. 2008, 130, 5020. doi: 10.1021/ja7111788 pmid: 18355007
[55]	Mace, N.; Thornton, A. R.; Blakey, S. B. Angew. Chem., Int. Ed. 2013, 52, 5836. doi: 10.1002/anie.201301087
[56]	Hong, K.; Su, H.; Pei, C.; Lv, X.; Hu, W.; Qiu, L.; Xu, X. Org. Lett. 2019, 21, 3328. doi: 10.1021/acs.orglett.9b01074
[57]	Hong, K.; Zhou, S. Hu, W.; Xu, X. Org. Chem. Front. 2020, 7, 1327. doi: 10.1039/D0QO00294A
[58]	Thornton, A. R.; Martin, V. I.; Blakey, S. B. J. Am. Chem. Soc. 2009, 131, 2434. doi: 10.1021/ja809078d pmid: 19193003
[59]	Brawn, R. A.; Zhu, K.; Panek, J. S. Org. Lett. 2014, 16, 74. doi: 10.1021/ol403035g pmid: 24328560
[60]	Rodríguez, M. R.; Beltrán, A.; Mudarra, A. L.; Alvarez, E.; Maseras, F.; Díaz-Requejo, M. M.; Pérez, P. J. Angew. Chem., Int. Ed. 2017, 56, 12842. doi: 10.1002/anie.201705664
[61]	Pan, D.; Wei, Y.; Shi, M. Org. Lett. 2018, 20, 84. doi: 10.1021/acs.orglett.7b03425
[62]	Pan, D.; Wei, Y.; Shi, M. Org. Lett. 2017, 19, 3584. doi: 10.1021/acs.orglett.7b01558
[63]	Pan, D.; Wei, Y.; Shi, M. Org. Chem. Front. 2019, 6, 1123. doi: 10.1039/C9QO00050J
[64]	Roy, S.; Khatua, H.; Das, S. K.; Chattopadhyay, B. Angew. Chem., Int. Ed. 2019, 58, 11439. doi: 10.1002/anie.v58.33