N-烷基胺类作为多功能砌块在氧化偶联反应中的应用

doi:10.6023/cjoc202009034

摘要/Abstract

N-烷基胺的氧化官能团化是形成碳-碳键和碳-杂原子键的最直接和通用的策略之一. 近年来, N-烷基胺类作为多功能砌块在交叉脱氢偶联(CDC)反应中取得了长足发展. 基于N-烷基胺的不同角色, 总结了近年来它们在氧化偶联反应中的应用进展.

关键词: N-烷基胺, N,N-二甲基苯胺, 四氢异喹啉, 交叉脱氢偶联反应

The oxidative functionalization of N-alkylamines is one of the most direct and versatile strategies for the formation of C—C and C-heteroatom bonds. In recent years,N-alkylamines as multifunctional blocks have made great progress in cross- dehydrogenation-coupling (CDC) reactions. The recent progress in the application of N-alkylamines is summarized on the basis of different roles in oxidative coupling reactions.

Key words: N-alkylamines, N,N-dimethylamine, tetrahydroisoquinoline, cross-dehydrogenative-coupling reaction

引用此文

陈缘, 夏立静, 常怡婷, 马武珍, 王彬. N-烷基胺类作为多功能砌块在氧化偶联反应中的应用[J]. 有机化学, 2021, 41(5): 1851-1877.

Yuan Chen, Lijing Xia, Yiting Chang, Wuzhen Ma, Bin Wang. Application of N-Alkyl Amines as Versatile Building Blocks in Oxidative Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1851-1877.

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

分享此文

图/表 46

Scheme 1. Copper-catalyzed CDC reaction of TIHQs and nitroalkanes

Scheme 2. PhI(OAc)2-mediated CDC reaction of tertiary amines

Scheme 3. Trifluoromethylation of TIHQs

Scheme 4. Mechanism for the Cu-catalyzed reaction of THIQs

Scheme 5. VO(acac)2-promoted CDC reaction of THIQs

Scheme 6. AuNPore-catalyzed CDC reactions of THIQs

Scheme 7. Tropylium salt-mediated reaction

Scheme 8. Trichloromethylation of tertiary amines

Scheme 9. Asymmetric CDC reaction between N-phenyl THIQs and ketones

Scheme 10. Synthesis of tetrahydroquinolines

Scheme 11. Dehydrogenative [4+2] intramolecular cycloaddition of tertiary anilines and enamides

Scheme 12. Reaction of arylboronic acid and THIQs

Scheme 13. Reaction of N-heterocycles and N,N-dimethyl- anilines

Scheme 14. FeCl3-catalyzed aerobic oxidation of tertiary anilines

Scheme 15. Metal-free CDC reaction of THIQs with I2/TBHP or I2/O2

Scheme 16. Asymmetric synthesis of 2-substituted-tetrahydro- isoquinolin-1-yl glycines

Scheme 17. Oxidative cross-dehydrogenative coupling between N-aryl tetrahydroisoquinolins and 5H-oxazol-4-ones

Scheme 18. 2D-MoS2-photocatalyzed CDC reaction of TIHPs

Scheme 19. Amidation of tertiary amines

Scheme 20. N-Alkylation and C(3)-acylation of indoles

Scheme 21. Synthesis of α-aminophosphonates

Scheme 22. Synthesis of the methylene-bridged bis-1,3- dicarbonyl derivatives

Scheme 23. Intramolecular dehydrogenative coupling reaction

Scheme 24. Rearrangement of propargylic amines

Scheme 25. Intramolecular cyclization for synthesis of acylated indoles

Scheme 26. Synthesis of 3-aroylindoles

Scheme 27. Synthesis of multisubstituted benzimidazoles

Scheme 28. Synthesis of α-(acyloxy)-β-amino ketones or α,β-diamino ketones

Scheme 29. Transformation using alkyl and aryl halides activated via α-aminoalkyl radical-mediated XAT

Scheme 30. Metal-free visible-light induced CDC of tertiary amines with diazo compounds

Scheme 31. [4+2] Cycloaddition of N-aryl tetrahydroisoquinolines with crotonaldehyde

Scheme 32. Iron-catalyzed α-C—H alkylation of N-methylaniline

Scheme 33. Cu(I)-catalyzed amidation/imidation of N-arylgly- cine ester derivatives

Scheme 34. C―H bond functionalization of allylbenzamides

Scheme 35. Ru-catalyzed indole formylation

Scheme 36. C(3)-formylation of indole

Scheme 37. Synthesis of imines from secondary amines

Scheme 38. Synthesis of oxazoles from benzylamines and aryl alkenes

Scheme 39. Synthesis of imidazo[1,5-a]pyridines

Scheme 40. Copper-promoted double oxidative C-H amination

Scheme 41. Synthesis of oxazoles through a Cu-mediated aerobic oxidative dehydrogenative annulation

Scheme 42. Synthesis of benzimidazole and N-benzylidene- benzylamines

Scheme 43. Pd-catalyzed deamination and cyclization of benzylamine with iodoarenes

Scheme 44. Deamination and condsention of benzylamines with N,N-dimethylaniline derivatives

Scheme 45. Deamination and coupling reaction of benzylamine

Scheme 46. Deamination and cyclization of benzylamines

参考文献 106

[1]	(a) Murahashi, S.-I.; Zhang, D. Chem. Soc. Rev. 2008, 37, 1490. doi: 10.1039/b706709g
	(b) Li, C. J. Acc. Chem. Res. 2009, 42, 335. doi: 10.1021/ar800164n
	(c) Scheuermann, C. J. Chem.-Asian J. 2010, 5, 436. doi: 10.1002/asia.v5:3
	(d) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068. doi: 10.1039/c1cs15082k
	(e) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. doi: 10.1021/cr100280d
	(f) Jones, K. M.; Klussmann, M. Synlett 2012, 23, 159.
	(g) Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem., Int. Ed. 2014, 53, 74.
	(h) Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170. doi: 10.1021/cr100209d
[2]	Li, Y.; Ma, L.; Li, Z. Chin. J. Org. Chem. 2013, 33, 704. (in Chinese). doi: 10.6023/cjoc201301065
	(李远明, 马丽娜, 李志平, 有机化学, 2013, 33, 704.) doi: 10.6023/cjoc201301065
[3]	Edwards, P. M.; Schafer, L. L. Chem. Commun. 2018, 54, 12543. doi: 10.1039/C8CC06445H
[4]	Ouyang, K.; Hao, W.; Zhang, W. X.; Xi, Z. Chem. Rev. 2015, 115, 12045. doi: 10.1021/acs.chemrev.5b00386
[5]	Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672. doi: 10.1021/ja050058j
[6]	Tsang, A. S. K.; Todd, M. H. Tetrahedron Lett. 2009, 50, 1199.
[7]	Shu, X. Z.; Xia, X. F.; Yang, Y. F.; Ji, K. G.; Liu, X. Y.; Liang, Y. M. J. Org. Chem. 2009, 74, 7464. doi: 10.1021/jo901583r
[8]	Chu, L.; Qing, F.-L. Chem. Commun. 2010, 46, 6285. doi: 10.1039/c0cc01073a
[9]	Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Farès, C.; Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106. doi: 10.1021/ja201610c
[10]	Jones, K. M.; Karier, P.; Klussmann, M. ChemCatChem 2012, 4, 51. doi: 10.1002/cctc.v4.1
[11]	Huang, W.; Ni, C.; Zhao, Y.; Hu, J. New J. Chem. 2013, 37, 1684. doi: 10.1039/C2NJ40842B
[12]	Ho, H. E.; Ishikawa, Y.; Asao, N.; Yamamoto, Y.; Jin, T. Chem. Commun. 2015, 51, 12764. doi: 10.1039/C5CC04856G
[13]	Kim, Y. H.; Gil, M. G.; Kim, D. Y. Bull. Korean Chem. Soc. 2017, 38, 1499. doi: 10.1002/bkcs.2017.38.issue-12
[14]	Oss, G.; de Vos, S. D.; Luc, K. N. H.; Harper, J. B.; Nguyen, T. V. J. Org. Chem. 2018, 83, 1000. doi: 10.1021/acs.joc.7b02584
[15]	Gil-Negrete, J. M.; Pérez Sestelo, J.; Sarandeses, L. A. J. Org. Chem. 2019, 84, 9778. doi: 10.1021/acs.joc.9b00928
[16]	Patil, M. R.; Dedhia, N. P.; Kapdi, A. R.; Kumar, A. V. J. Org. Chem. 2018, 83, 4477. doi: 10.1021/acs.joc.8b00203
[17]	Xu, C.; Zhu, Z.; Wang, Y.; Jing, Z.; Gao, B.; Zhao, L.; Dong, W. K. J. Org. Chem. 2019, 84, 2234. doi: 10.1021/acs.joc.8b03238
[18]	Yang, Q.; Zhang, L.; Ye, C.; Luo, S.; Wu, L. Z.; Tung, C. H. Angew. Chem., Int. Ed. 2017, 56, 3694. doi: 10.1002/anie.201700572
[19]	Nishino, M.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 6447. doi: 10.1021/jo2011329
[20]	Zhao, M.-N.; Yu, L.; Hui, R.-R.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. ACS Catal. 2016, 6, 3473. doi: 10.1021/acscatal.6b00849
[21]	Ma, Y.; Zhang, G.; Zhang, J.; Yang, D.; Wang, R. Org. Lett. 2014, 16, 5358. doi: 10.1021/ol5025597
[22]	Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997. doi: 10.1021/ol047814v
[23]	Niu, M.; Yin, Z.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 3961. doi: 10.1021/jo800279j
[24]	Jin, X.; Yamaguchi, K.; Mizuno, N. RSC Adv. 2014, 4, 34712. doi: 10.1039/C4RA05105J
[25]	Sun, S.; Li, C.; Floreancig, P. E.; Lou, H.; Liu, L. Org Lett. 2015, 17, 1684. doi: 10.1021/acs.orglett.5b00447
[26]	Huang, T.; Liu, X.; Lang, J.; Xu, J.; Lin, L.; Feng, X. ACS Catal. 2017, 7, 5654. doi: 10.1021/acscatal.7b01912
[27]	Ma, L.; Shi, X.; Li, X.; Shi, D. Org. Chem. Front. 2018, 5, 3515. doi: 10.1039/C8QO01028E
[28]	Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968. doi: 10.1021/ja0516054
[29]	Baslé, O.; Li, C.-J. Org. Lett. 2008, 10, 3661. doi: 10.1021/ol8012588
[30]	Huang, L.; Niu, T.; Wu, J.; Zhang, Y. J. Org. Chem. 2011, 76, 1759. doi: 10.1021/jo1023975
[31]	Ratnikov, M. O.; Xu, X.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 9475. doi: 10.1021/ja402479r
[32]	Singh, A.; Arora, A.; Weaver, J. D. Org. Lett. 2013, 15, 5390. doi: 10.1021/ol402751j
[33]	Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett. 2013, 15, 1092. doi: 10.1021/ol4001153
[34]	Zhou, S.; Wang, J.; Lin, D.; Zhao, F.; Liu, H. J. Org. Chem. 2013, 78, 11204. doi: 10.1021/jo401510b
[35]	Liu, X.; Zhang, J.; Ma, S.; Ma, Y.; Wang, R. Chem. Commun. 2014, 50, 15714. doi: 10.1039/C4CC04508D
[36]	Yu, C.; Patureau, F. W. Angew. Chem., Int. Ed. 2018, 57, 11807. doi: 10.1002/anie.v57.36
[37]	Kibriya, G.; Bagdi, A. K.; Hajra, A. J. Org. Chem. 2018, 83, 10619. doi: 10.1021/acs.joc.8b01433
[38]	Girish, Y. R.; Jaiswal, K.; Prakash, P.; De, M. Catal. Sci. Technol. 2019, 9, 1201. doi: 10.1039/C8CY02532K
[39]	Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2007, 9, 3813. doi: 10.1021/ol701715m
[40]	Li, L. T.; Li, H. Y.; Xing, L. J.; Wen, L. J.; Wang, P.; Wang, B. Org. Biomol. Chem. 2012, 10, 9519. doi: 10.1039/c2ob26636a
[41]	Singh, S. K.; Chandna, N.; Jain, N. Org. Lett. 2017, 19, 1322. doi: 10.1021/acs.orglett.7b00125
[42]	Lao, Z.-Q.; Zhong, W.-H.; Lou, Q.-H.; Li, Z.-J.; Meng, X.-B. Org. Biomol. Chem. 2012, 10, 7869. doi: 10.1039/c2ob26430g
[43]	Zhao, Y.; Zeng, J.; Xia, W. Chin. J. Org. Chem. 2020, 40, 133. (in Chinese). doi: 10.6023/cjoc201907002
	(赵亚婷, 曾俊杰, 夏吾炯, 有机化学, 2020, 40, 133.) doi: 10.6023/cjoc201907002
[44]	Dhineshkumar, J.; Samaddar, P.; Prabhu, K. R. ACS Omega. 2017, 2, 4885. doi: 10.1021/acsomega.7b00881 pmid: 31457767
[45]	Lin, B.; Shi, S.; Lin, R.; Cui, Y.; Fang, M.; Tang, G.; Zhao, Y. J. Org. Chem. 2018, 83, 6754. doi: 10.1021/acs.joc.8b00674
[46]	Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176. doi: 10.1021/ol901751c
[47]	Yoo, W.-J.; Tanoue, A.; Kobayashi, S. Chem.-Asian J. 2012, 7, 2764. doi: 10.1002/asia.201200807
[48]	Xing, L. J.; Wang, X. M.; Li, H. Y.; Zhou, W.; Kang, N.; Wang, P.; Wang, B. RSC Adv. 2014, 4, 26783. doi: 10.1039/C4RA04419C
[49]	Xing, L. J.; Lu, T.; Fu, W. L.; Lou, M. M.; Chen, B.; Wang, Z. S.; Jin, Y.; Li, D.; Wang, B. Adv. Synth. Catal. 2015, 357, 3076. doi: 10.1002/adsc.201500691
[50]	Guo, S.; Gong, J.; Lu, L.; Zhu, Z.; Cai, H. Chin. J. Org. Chem. 2015, 35, 1348. (in Chinese). doi: 10.6023/cjoc201412035
	(郭生梅, 龚久涵, 卢林, 朱正, 蔡琥, 有机化学, 2015, 35, 1348.) doi: 10.6023/cjoc201412035
[51]	Zheng, Y.; Mao, J.; Chen, J.; Rong, G.; Liu, D.; Yan, H.; Chi, Y.; Xu, X. RSC Adv. 2015, 5, 50113. doi: 10.1039/C5RA06773A
[52]	Volvoikar, P. S.; Tilve, S. G. Org. Lett. 2016, 18, 892. doi: 10.1021/acs.orglett.5b03392
[53]	Wang, S.; Li, X.; Zang, J.; Liu, M.; Zhang, S.; Jiang, G.; Ji, F. J. Org. Chem. 2020, 85, 2672. doi: 10.1021/acs.joc.9b02771
[54]	Tian, J. S.; Loh, T. P. Angew. Chem., Int. Ed. 2010, 49, 8417. doi: 10.1002/anie.201003646
[55]	Chen, M.; Peng, J.; Mao, T.; Huang, J. Org. Lett. 2014, 16, 6286. doi: 10.1021/ol5029805
[56]	Gogoi, A.; Guin, S.; Rout, S. K.; Patel, B. K. Org. Lett. 2013, 15, 1802. doi: 10.1021/ol400692b
[57]	Paladugu, S.; Mainkar, P. S.; Chandrasekhar, S. ACS Omega 2018, 3, 4289. doi: 10.1021/acsomega.8b00476 pmid: 31458657
[58]	Li, B.; Xu, H.; Wang, H.; Wang, B. ACS Catal. 2016, 6, 3856. doi: 10.1021/acscatal.6b00311
[59]	Xue, D.; Long, Y. Q. J. Org. Chem. 2014, 79, 4727. doi: 10.1021/jo5005179
[60]	Zhang, T. S.; Hao, W. J.; Wang, N. N.; Li, G.; Jiang, D. F.; Tu, S. J.; Jiang, B. Org. Lett. 2016, 18, 3078. doi: 10.1021/acs.orglett.6b01189
[61]	Guerrero, I.; San Segundo, M.; Correa, A. Chem. Commun. 2018, 54, 1627. doi: 10.1039/C7CC09872C
[62]	Constantin, T.; Zanini, M.; Regni, A.; Sheikh, N. S.; Julia, F.; Leonori, D. Science 2020, 367, 1021. doi: 10.1126/science.aba2419
[63]	Xiao, T.; Li, L.; Lin, G.; Mao, Z. W.; Zhou, L. Org Lett. 2014, 16, 4232. doi: 10.1021/ol501933h
[64]	Wang, N.-N.; Hao, W.-J.; Zhang, T.-S.; Li, G.; Wu, Y.-N.; Tu, S.-J.; Jiang, B. Chem. Commun. 2016, 52, 5144. doi: 10.1039/C6CC00816J
[65]	Zhang, T. S.; Zhao, Q.; Hao, W. J.; Tu, S. J.; Jiang, B. Chem.-Asian J. 2019, 14, 1042. doi: 10.1002/asia.v14.7
[66]	Wu, X.; Chen, D.-F.; Chen, S.-S.; Zhu, Y.-F. Eur. J. Org. Chem. 2015, 2015, 468.
[67]	Li, Z. L.; Sun, K. K.; Wu, P. Y.; Cai, C. J. Org. Chem. 2019, 84, 6830. doi: 10.1021/acs.joc.9b00625
[68]	Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A. Org. Lett. 2009, 11, 1607. doi: 10.1021/ol900298e
[69]	Daggupati, R. V.; Malapaka, C. Org. Chem. Front. 2018, 5, 788. doi: 10.1039/C7QO00851A
[70]	Ranjith, J.; Krishna, P. R. Tetrahedron Lett. 2019, 60, 1437. doi: 10.1016/j.tetlet.2019.04.041
[71]	Wu, W.; Su, W. J. Am. Chem. Soc. 2011, 133, 11924. doi: 10.1021/ja2048495
[72]	Li, L. T.; Huang, J.; Li, H. Y.; Wen, L. J.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 5187. doi: 10.1039/c2cc31578e
[73]	Wang, Z.; Zhang, L.; Zhang, F.; Wang, B. Chin. J. Org. Chem. 2019, 39, 2323. (in Chinese). doi: 10.6023/cjoc201903077
	(王震, 张玲, 张富赓, 王彬, 有机化学, 2019, 39, 2323.) doi: 10.6023/cjoc201903077
[74]	Sonobe, T.; Oisaki, K.; Kanai, M. Chem. Sci. 2012, 3, 3249. doi: 10.1039/c2sc20699d
[75]	Wan, C.; Zhang, J.; Wang, S.; Fan, J.; Wang, Z. Org. Lett. 2010, 12, 2338. doi: 10.1021/ol100688c
[76]	Yang, S.; Yang, Y.; Li, F.; Liu, X. Tetrahedron Lett. 2020, 61, 151846. doi: 10.1016/j.tetlet.2020.151846
[77]	Jiang, H.; Huang, H.; Cao, H.; Qi, C. Org. Lett. 2010, 12, 5561. doi: 10.1021/ol1023085
[78]	Chen, Z.; Li, H.; Dong, W.; Miao, M.; Ren, H. Org. Lett. 2016, 18, 1334. doi: 10.1021/acs.orglett.6b00277
[79]	Zhang, X.; He, Y.; Li, J.; Wang, R.; Gu, L.; Li, G. J. Org. Chem. 2019, 84, 8225. doi: 10.1021/acs.joc.9b00283
[80]	Yan, Y.; Zhang, Y.; Zha, Z.; Wang, Z. Org. Lett. 2013, 15, 2274. doi: 10.1021/ol4008487
[81]	Chandra Mohan, D.; Nageswara Rao, S.; Ravi, C.; Adimurthy, S. Org. Biomol. Chem. 2015, 13, 5602. doi: 10.1039/C5OB00381D
[82]	Qian, P.; Yan, Z.; Zhou, Z.; Hu, K.; Wang, J.; Li, Z.; Zha, Z.; Wang, Z. Org. Lett. 2018, 20, 6359. doi: 10.1021/acs.orglett.8b02578
[83]	Qian, P.; Yan, Z.; Zhou, Z.; Hu, K.; Wang, J.; Li, Z.; Zha, Z.; Wang, Z. J. Org. Chem. 2019, 84, 3148. doi: 10.1021/acs.joc.8b03014
[84]	Li, M.; Xie, Y.; Ye, Y.; Zou, Y.; Jiang, H.; Zeng, W. Org. Lett. 2014, 16, 6232. doi: 10.1021/ol503165b
[85]	Wang, H.; Xu, W.; Wang, Z.; Yu, L.; Xu, K. J. Org. Chem. 2015, 80, 2431. doi: 10.1021/jo5027723
[86]	(a) Tan, Z.; Zhao, H.; Zhou, C.; Jiang, H.; Zhang, M. J. Org. Chem. 2016, 81, 9939. doi: 10.1021/acs.joc.6b02117
	(b) Li, Z.; Wu, S.-S.; Luo, Z.-G.; Liu, W.-K.; Feng, C.-T.; Ma, S.-T. J. Org. Chem. 2016, 81, 4386. doi: 10.1021/acs.joc.6b00569
[87]	Xu, Z.; Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2012, 51, 11367. doi: 10.1002/anie.201206382
[88]	Pan, J.; Li, X.; Qiu, X.; Luo, X.; Jiao, N. Org. Lett. 2018, 20, 2762. doi: 10.1021/acs.orglett.8b00992
[89]	Wang, X.; Qiu, X.; Wei, J.; Liu, J.; Song, S.; Wang, W.; Jiao, N. Org. Lett. 2018, 20, 2632. doi: 10.1021/acs.orglett.8b00840
[90]	Xu, W.; Jin, Y.; Liu, H.; Jiang, Y.; Fu, H. Org. Lett. 2011, 13, 1274. doi: 10.1021/ol1030266
[91]	Modi, A.; Ali, W.; Mohanta, P. R.; Khatun, N.; Patel, B. K. ACS Sustainable Chem. Eng. 2015, 3, 2582. doi: 10.1021/acssuschemeng.5b00817
[92]	Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2012, 14, 6068. doi: 10.1021/ol302955u
[93]	Salfeena, C. T. F.; Jalaja, R.; Davis, R.; Suresh, E.; Somappa, S. B. ACS Omega 2018, 3, 8074. doi: 10.1021/acsomega.8b01017
[94]	Nguyen, T. B.; Ermolenko, L.; Dean, W. A.; Al-Mourabit, A. Org. Lett. 2012, 14, 5948. doi: 10.1021/ol302856w
[95]	Dong, C. P.; Higashiura, Y.; Marui, K.; Kumazawa, S.; Nomoto, A.; Ueshima, M.; Ogawa, A. ACS Omega. 2016, 1, 799. doi: 10.1021/acsomega.6b00235
[96]	Gopalaiah, K.; Saini, A.; Devi, A. Org. Biomol. Chem. 2017, 15, 5781. doi: 10.1039/C7OB01159H
[97]	Kumar, M. R.; Park, A.; Park, N.; Lee, S. Org. Lett. 2011, 13, 3542. doi: 10.1021/ol201409j
[98]	Xu, C.; Jia, F.-C.; Zhou, Z.-W.; Zheng, S.-J.; Li, H.; Wu, A.-X. J. Org. Chem. 2016, 81, 3000. doi: 10.1021/acs.joc.5b02843
[99]	Nguyen, T. B.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2012, 14, 4274. doi: 10.1021/ol3020368
[100]	Ravi Kumar, D.; Satyanarayana, G. Org. Lett. 2015, 17, 5894. doi: 10.1021/acs.orglett.5b03077
[101]	Dong, C.-P.; Kodama, S.; Uematsu, A.; Nomoto, A.; Ueshima, M.; Ogawa, A. J. Org. Chem. 2017, 82, 12530. doi: 10.1021/acs.joc.7b02296
[102]	Gong, L.; Xing, L. J.; Xu, T.; Zhu, X. P.; Zhou, W.; Kang, N.; Wang, B. Org. Biomol. Chem. 2014, 12, 6557. doi: 10.1039/C4OB01025F
[103]	Sharma, R.; Abdullaha, M.; Bharate, S. B. J. Org. Chem. 2017, 82, 9786. doi: 10.1021/acs.joc.7b00856
[104]	Majji, G.; Rajamanickam, S.; Khatun, N.; Santra, S. K.; Patel, B. K. J. Org. Chem. 2015, 80, 3440. doi: 10.1021/jo502903d
[105]	Kim, K.; Kim, H. Y.; Oh, K. Org. Lett. 2019, 21, 6731. doi: 10.1021/acs.orglett.9b02348
[106]	Kirinde Arachchige, P.T.. Yi, C. S. Org. Lett. 2019, 21, 3337. doi: 10.1021/acs.orglett.9b01082