Recent Advances in C—H Bond Functionalization under Mechanochemical Conditions

doi:10.6023/cjoc202106046

Abstract

Mechanochemistry has received increasing attention in the past decade. Among which, the mechanochemical C—H bond functionalization has emerged as a hot research topic. In comparison with the traditional solution-based organic reactions, the mechanochemical transformation features solvent-less conditions and short reaction time, constituting a green and efficient synthetic method in the modern chemical society. Notably, given the outstanding features, some long-standing challenges in the previous solution-based reactions could be well-solved by mechanochemical methods. Therefore, a timely comprehensive overview to recognize the present status of the mechanochemical C—H bond functionalization is of great importance to stimulate the development of more efficient synthetic methods. In this review, the state of the art for mechanochemical C—H bond transformation is presented. The limitation in this research field is also analyzed and the outlook of this area is prospected.

Key words: mechanochemistry, C—H bond functionalization, ball milling, solvent-free, green chemistry

Cite this article

Kun Zhou, Yangjie Mao, Fengwei Wu, Shaojie Lou, Danqian Xu. Recent Advances in C—H Bond Functionalization under Mechanochemical Conditions[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4623-4638.

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Fig. & Tab. 43

Figure 1. Number of peer-reviewed papers on mechanochemical C—H bond functionalization (2011~2020)

Scheme 1. Mechanochemical solid-state C—H bond activation of azobenzenes

Scheme 2. Mechanosynthesis of aryl-Au complexes

Scheme 3. Mechanochemical Rh catalyzed C—H bond olefination of acetanilides

Scheme 4. Mechanochemical selective synthesis of 3-vinylindoles or β,β-diindolyl propionates

Scheme 5. Proposed mechanism of mechanochemical selective synthesis of 3-vinylindoles and β,β-diindolyl propionates

Scheme 6. Mechanochemical alkenylation of furans or thiophenes

Scheme 7. Mechanochemical alkenylation and heteroarylation of indazoles

Scheme 8. Mechanosynthesis of an intermediate of CFI-400945 and YC-1

Scheme 9. Mechanochemical Mn catalyzed C—H bond alkenylation of indoles

Scheme 10. Mechanochemical selective C—H bond alkynylation of indoles

Scheme 11. Mechanochemical Pd catalyzed cross dehydrogenation coupling arylation

Scheme 12. KIE experiments for mechanochemical Pd catalyzed C—H bond arylations

Scheme 13. Mechanochemical Pd catalyzed C—H bond arylation of indoles

Scheme 14. Mechanochemical Co catalyzed C—H bond allylation of indoles

Scheme 15. Mechanochemical Rh catalyzed C—H bond methylation

Scheme 16. Mechanochemical Cu catalyzed decarboxylative acylation of indoles with α-ketonates

Scheme 17. Mechanochemical Cu catalyzed CDC reaction

Scheme 18. Mecheanochemical asymmetric C(sp3)—H CDC reaction of tetrahydroisoquinolines

Scheme 19. Mechanochemical Ir catalyzed C—H bond sulfonamidation

Scheme 20. Mechanochemical Rh catalyzed C—H bond amidation with oxazolidinediones

Scheme 21. Mechanochemical Co catalyzed C—H bond amidation

Scheme 22. Mechanochemical Co catalyzed ferrocene C—H bond amidation

Scheme 23. Mechanochemical Rh-catalyzed C—H bond amidation of N-nitrosoanilines

Scheme 24. Mechanochemical Rh-catalyzed C(sp3)—H bond amination

Scheme 25. Mechanochemical Rh-catalyzed halogenation of 2-phenylpyridine

Scheme 26. Mechanochemical Pd catalyzed C—H bond iodination

Scheme 27. Plausible mechanism of the mechanochemical C—H bond iodination

Scheme 28. Mechanochemical Ir-catalyzed C—H bond borylation

Scheme 29. Mechanochemical Pd catalyzed C—H bond etherification

Scheme 30. Mechanochemical cross-coupling reactions of thiazoles with organophosphorus compounds

Scheme 31. Mechanochemical synthesis of indoles under Rh catalysis

Scheme 32. Mechanochemical synthesis of 1,2-benzothiazines from sulfonimidamides under Ir catalysis

Scheme 33. Amidation of aldehydes with N-chloramines under neat conditions or ball milling conditions

Scheme 34. Proposed mechanism for the amide formation from aldehyde and N—Cl amine

Scheme 35. Mechanochemical synthesis of amides from aldehydes and amines

Scheme 36. Radical C—H functionalization under transition metal catalysis or photocatalysis

Scheme 37. Mechano-redox C—H bond arylation of heterocycles

Scheme 38. Mechanochemical solid-state radical C—H bond trifluoromethylation in the presence of piezoelectric materials

Scheme 39. Radical C—H bond trifluoromethylation under different conditions

Scheme 40. Control experiments in the mechano-redox C—H bond trifluoromethylation

Scheme 41. Mechanochemical I2 catalyzed C—H bond sulfuration of indoles with disulfides

Scheme 42. Mechanochemical aryl C—H bond thiocyanation

References 64

[1]	Boldyreva, E. Chem. Soc. Rev. 2013, 42, 7719. doi: 10.1039/c3cs60052a pmid: 23864028
[2]	(a) Fu, Z. Eng. Chem. Metall. 1988, 9, 61. (in Chinese)
	( 傅正义, 化工冶金, 1988, 9, 61.)
	(b) Ma, Z.; Li, H.; Zhang, Z.; Ma, Y. Non-Ferrous Min. Metall. 2004, 20, 98. (in Chinese)
	( 马正先, 李慧, 张在美, 马云东, 有色矿治, 2004, 20, 98.)
	(c) Rong, H.; Fang, Y. Guangdong Chem. Ind. 2006, 33, 33. (in Chinese)
	( 荣华伟, 方莹, 广东化工, 2006, 33, 33.)
	(d) Zhang, S. Y.; Geng, M. P. Yunnan Metall. 2006, 35, 46. (in Chinese)
	( 张颂阳, 耿茂鹏, 云南冶金, 2006, 35, 46.)
[3]	(a) Peters, K. Frankfurt 1962, 31.
	(b) Zhang, W.; Wang, S. Min. Proc. Equip. 2003, 8, 50. (in Chinese)
	张伟, 王树林, 矿山机械, 2003, 8, 50).
	(c) LI, L.; Chen, G. China Ceram. Ind. 2003, 10, 52. (in Chinese)
	( 李玲, 陈国华, 中国陶瓷工业, 2003, 10, 52.)
	(d) Yin, Y.; Chen, Y. Metall. Collect. 2008, 178, 37. (in Chinese)
	( 尹艳红, 陈应禄, 冶金丛刊, 2008, 178, 37.)
	(e) Xu, H.; Wang, F.; Xie, Y. New Chem. Mater. 2009, 37, 7. (in Chinese)
	( 许红娅, 王芬, 解宇星, 化工新型材料, 2009, 37, 7.)
	(f) Fang, G.; Shen, K.; Li, X. China Pulp Paper 2020, 39, 55. (in Chinese)
	( 房桂干, 沈葵忠, 李晓亮, 中国造纸, 2020, 39, 55.)
[4]	(a) Gilman, J. J. Science 1996, 274, 65. doi: 10.1126/science.274.5284.65 pmid: 31059243
	(b) Hickenboth, C. R.; Moore, J. S.; White, S. R.; Sottos, N. R.; Baudry, J.; Wilson, S. R. Nature 2007, 446, 423. doi: 10.1038/nature05681 pmid: 31059243
	(c) Caruso, M. M.; Davis, D. A.; Shen, Z.; Odom, S. A.; Sottos, N. R.; White, S. R.; Moore, J. S. Chem. Rev. 2009, 109, 5755. doi: 10.1021/cr9001353 pmid: 31059243
	(d) Belenguer, A. M.; Friščić, T.; Day, G. M.; Sanders, J. K. M. Chem. Sci. 2011, 2, 696. doi: 10.1039/c0sc00533a pmid: 31059243
	(e) James, S. L.; Adams, C. J.; Bolm, C.; Braga, D.; Collier, P.; Friscic, T.; Grepioni, F.; Harris, K. D.; Hyett, G.; Jones, W.; Krebs, A.; Mack, J.; Maini, L.; Orpen, A. G.; Parkin, I. P.; Shearouse, W. C.; Steed, J. W.; Waddell, D. C. Chem. Soc. Rev. 2012, 41, 413. doi: 10.1039/C1CS15171A pmid: 31059243
	(f) Hernandez, J. G.; Bolm, C. J. Org. Chem. 2017, 82, 4007. doi: 10.1021/acs.joc.6b02887 pmid: 31059243
	(g) Andersen, J. M.; Mack, J. Chem. Sci. 2017, 8, 5447. doi: 10.1039/c7sc00538e pmid: 31059243
	(h) Bolm, C.; Hernandez, J. G. ChemSusChem 2018, 11, 1410. doi: 10.1002/cssc.v11.9 pmid: 31059243
	(i) Howard, J. L.; Brand, M. C.; Browne, D. L. Angew. Chem., Int. Ed. 2018, 57, 16104. doi: 10.1002/anie.v57.49 pmid: 31059243
	(j) Howard, J. L.; Cao, Q.; Browne, D. L. Chem. Sci. 2018, 9, 3080. doi: 10.1039/C7SC05371A pmid: 31059243
	(k) Andersen, J.; Mack, J. Green Chem. 2018, 20, 1435. doi: 10.1039/C7GC03797J pmid: 31059243
	(l) Beillard, A.; Bantreil, X.; Metro, T. X.; Martinez, J.; Lamaty, F. Chem. Rev. 2019, 119, 7529. doi: 10.1021/acs.chemrev.8b00479 pmid: 31059243
	(m) Colacino, E.; Porcheddu, A.; Charnay, C.; Delogu, F. React. Chem. Eng. 2019, 4, 1179. doi: 10.1039/c9re00069k pmid: 31059243
	(n) Friscic, T.; Mottillo, C.; Titi, H. M. Angew. Chem., Int. Ed. 2020, 59, 1018. doi: 10.1002/anie.v59.3 pmid: 31059243
	(o) Wang, G.-W. Chin. J. Chem. 2021, 39, 1797. doi: 10.1002/cjoc.v39.7 pmid: 31059243
[5]	(a) Zhu, S. E.; Li, F.; Wang, G.-W. Chem. Soc. Rev. 2013, 42, 7535. doi: 10.1039/c3cs35494f
	(b) Wang, G.-W. Chem. Soc. Rev. 2013, 42, 7668. doi: 10.1039/c3cs35526h
	(c) Wang, N. N.; Wang, G.-W. Prog. Chem. 2020, 32, 1076. (in Chinese)
	( 王娜娜, 王官武, 化学进展, 2020, 32, 1076). doi: 10.7536/PC200448
	(d) Kubota, K.; Ito, H. Trends Chem. 2020, 2, 1066. doi: 10.1016/j.trechm.2020.09.006
	(e) Wang, H.; Ying, P.; Yu, J.; Su, W. Chin. J. Org. Chem. 2021, 41, 1897. (in Chinese)
	( 王浩, 应娉, 俞静波, 苏为科, 有机化学, 2021, 41, 1897.) doi: 10.6023/cjoc202009053
[6]	(a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. doi: 10.1021/cr00039a007
	(b) Nielsen, S. F.; Peters, D.; Axelsson, O. Synth. Commun. 2000, 30, 3501. doi: 10.1080/00397910008087262
[7]	(a) Shao, Q.; Jiang, Z.; Su, W. Tetrahedron Lett. 2018, 59, 2277. doi: 10.1016/j.tetlet.2018.04.078
	(b) Cao, Q.; Nicholson, W. I.; Jones, A. C.; Browne, D. L. Org. Biomol. Chem. 2019, 17, 1722. doi: 10.1039/C8OB01781F
[8]	Tullberg, E.; Peters, D.; Frejd, T. J. Org. Chem. 2004, 689, 3778.
[9]	Fulmer, D. A.; Shearouse, W. C.; Medonza, S. T.; Mack, J. Green Chem. 2009, 11, 1821. doi: 10.1039/b915669k
[10]	(a) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507. doi: 10.1038/417507a pmid: 21428440
	(b) Godula, K.; Sames, D. Science 2006, 312, 67. pmid: 21428440
	(c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. doi: 10.1021/cr900184e pmid: 21428440
	(d) Ackermann, L. Chem. Rev. 2011, 111, 1315. doi: 10.1021/cr100412j pmid: 21428440
	(e) Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902. doi: 10.1039/c1cs15058h pmid: 21428440
	(f) Engle, K. M.; Mei, T. S.; Wang, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2011, 50, 1478. doi: 10.1002/anie.201005142 pmid: 21428440
	(g) Davies, H. M. L.; Bois, J. D.; Yu, J.-Q. Chem. Soc. Rev. 2011, 40, 1976. doi: 10.1039/c0cs00182a pmid: 21428440
	(h) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981. doi: 10.1021/cr100371y pmid: 21428440
[11]	(a) Hernandez, J. G. Chemistry 2017, 23, 17157.
	(b) Lukin, S.; Tireli, M.; Loncaric, I.; Barisic, D.; Sket, P.; Vrsaljko, D.; di Michiel, M.; Plavec, J.; K, U. Z.; Halasz, I. Chem. Commun. 2018, 54, 13216. doi: 10.1039/C8CC07853J
	(c) Zhao, S.; Li, Y.; Liu, C.; Zhao, Y. Tetrahedron Lett. 2018, 59, 317. doi: 10.1016/j.tetlet.2017.12.021
[12]	Juribasic, M.; Uzarevic, K.; Gracin, D.; Curic, M. Chem. Commun. 2014, 50, 10287. doi: 10.1039/C4CC04423A
[13]	Ingner, F. J. L.; Giustra, Z. X.; Novosedlik, S.; Orthaber, A.; Gates, P. J.; Dyrager, C.; Pilarski, L. T. Green Chem. 2020, 22, 5648. doi: 10.1039/D0GC02263B
[14]	Hermann, G. N.; Becker, P.; Bolm, C. Angew. Chem., Int. Ed. 2015, 54, 7414. doi: 10.1002/anie.v54.25
[15]	(a) Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982; doi: 10.1021/ja103834b
	(b) Yu, S.; Li, X. Org. Lett. 2014, 16, 1200. doi: 10.1021/ol5000764
[16]	Jia, K.; Yu, J.; Jiang, Z.; Su, W. J. Org. Chem. 2016, 81, 6049. doi: 10.1021/acs.joc.6b01138
[17]	Jia, K.; Jiang, Z.; Yu, J.; Hong, Z.; Su, W. Chin. J. Org. Chem. 2017, 37, 1473. (in Chinese) doi: 10.6023/cjoc201612047
	( 贾侃彦, 江之江, 俞静波, 洪子坤, 苏为科, 有机化学, 2017, 37, 1473.) doi: 10.6023/cjoc201612047
[18]	Yu, J.; Yang, X.; Wu, C.; Su, W. J. Org. Chem. 2020, 85, 1009. doi: 10.1021/acs.joc.9b02951
[19]	Sampson, P. B.; Liu, Y.; Patel, N. K.; Feher, M.; Forrest, B.; Li, S.-W.; Edwards, L.; Laufer, R.; Lang, Y.; Ban, F.; Awrey, D. E.; Mao, G.; Plotnikova, O.; Leung, G.; Hodgson, R.; Mason, J.; Wei, X.; Kiarash, R.; Green, E.; Qiu, W.; Chirgadze, N. Y.; Mak, T. W.; Pan, G.; Pauls, H. W. J. Med. Chem. 2014, 58, 130. doi: 10.1021/jm500537u
[20]	Tang, M.; Kong, Y.; Chu, B.; Feng, D. Adv. Synth. Catal. 2016, 358, 926. doi: 10.1002/adsc.v358.6
[21]	Das, D.; Bhosle, A. A.; Panjikar, P. C.; Chatterjee, A.; Banerjee, M. ACS Sustainable Chem. Eng. 2021, 8, 19105 doi: 10.1021/acssuschemeng.0c07465
[22]	(a) Nakao, Y.; Kanyiva, K. S.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2006, 128, 8146. doi: 10.1021/ja0623459 pmid: 25251735
	(b) Ding, Z.; Yoshikai, N. Angew. Chem., Int Ed. 2012, 51, 4698. pmid: 25251735
	(c) Sharma, S.; Han, S.; Shin, Y.; Mishra, N. K.; Oh, H.; Park, J.; Kwak, J. H.; Shin, B. S.; Jung, Y. H.; Kim, I. S. Tetrahedron Lett. 2014, 55, 3104. doi: 10.1016/j.tetlet.2014.04.001 pmid: 25251735
	(d) Liang, L.; Fu, S.; Lin, D.; Zhang, X. Q.; Deng, Y.; Jiang, H.; Zeng, W. J. Org. Chem. 2014, 79, 9472. doi: 10.1021/jo501460h pmid: 25251735
	(e) Shi, L.; Zhong, X.; She, H.; Lei, Z.; Li, F. Chem. Commun. 2015, 51, 7136. doi: 10.1039/C5CC00249D pmid: 25251735
[23]	Hermann, G. N.; Unruh, M. T.; Jung, S. H.; Krings, M.; Bolm, C. Angew. Chem., Int. Ed. 2018, 57, 10723. doi: 10.1002/anie.v57.33
[24]	(a) Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Bolz, J. T.; Simonsen, A. J. J. Org. Chem. 1996, 61, 6547. pmid: 11667518
	(b) Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346. doi: 10.1002/anie.v48:49 pmid: 11667518
	(c) Collins, K. D.; Lied, F.; Glorius, F. Chem. Commun. 2014, 50, 4459. doi: 10.1039/c4cc01141d pmid: 11667518
	(d) Feng, C.; Loh, T. P. Angew. Chem., Int. Ed. 2014, 53, 2722. doi: 10.1002/anie.201309198 pmid: 11667518
	(e) Xie, F.; Qi, Z.; Yu, S.; Li, X. J. Am. Chem. Soc. 2014, 136, 4780. doi: 10.1021/ja501910e pmid: 11667518
	(f) Zhang, Z. Z.; Liu, B.; Wang, C. Y.; Shi, B. F. Org. Lett. 2015, 17, 4094. doi: 10.1021/acs.orglett.5b02038 pmid: 11667518
	(g) Kang, D.; Hong, S. Org. Lett. 2015, 17, 1938. doi: 10.1021/acs.orglett.5b00641 pmid: 11667518
	(h) Caspers, L. D.; Finkbeiner, P.; Nachtsheim, B. J. Chemistry 2017, 23, 2748. pmid: 11667518
[25]	(a) Wang, X.; Leow, D.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 13864. doi: 10.1021/ja206572w pmid: 26308790
	(b) Xu, H.; Shang, M.; Dai, H. X.; Yu, J.-Q. Org. Lett. 2015, 17, 3830. doi: 10.1021/acs.orglett.5b01802 pmid: 26308790
	(c) Yang, Z.; Qiu, F. C.; Gao, J.; Li, Z. W.; Guan, B. T. Org. Lett. 2015, 17, 4316. doi: 10.1021/acs.orglett.5b02135 pmid: 26308790
[26]	Lou, S.-J.; Mao, Y.-J.; Xu, D.-Q.; He, J.-Q.; Chen, Q.; Xu, Z.-Y. ACS Catal. 2016, 6, 3890. doi: 10.1021/acscatal.6b00861
[27]	Das, D.; Bhutia, Z. T.; Chatterjee, A.; Banerjee, M. J. Org. Chem. 2019, 84, 10764. doi: 10.1021/acs.joc.9b01280
[28]	(a) Bosch, J.; Roca, Tomas; Armengol, M.; FernaÂndez-Forner, D. Tetrahedron 2001, 57, 1041. doi: 10.1016/S0040-4020(00)01091-7
	(b) Dinnell, K.; Chicchi, G. G.; Dhar, M. J.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Ridgill, M. P.; Rycroft, W.; Tsao, K. L.; Williams, A. R.; Swain, C. J. Biol. Med. Chem. Lett. 2001, 11, 1237. doi: 10.1016/S0960-894X(01)00183-4
	(c) Hartung, C. G.; Fecher, A.; Chapell, B.; Snieckus, V. Org. Lett. 2003, 5, 1899. doi: 10.1021/ol0344772
	(d) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873. doi: 10.1021/cr040639b
[29]	Jiang, X.; Chen, J.; Zhu, W.; Cheng, K.; Liu, Y.; Su, W.; Yu, C. J. Org. Chem. 2017, 82, 10665. doi: 10.1021/acs.joc.7b01695
[30]	(a) Barreiro, E. J.; Kümmerle, A. E.; Fraga, C. A. M. Chem. Rev. 2011, 111, 5215. doi: 10.1021/cr200060g pmid: 21631125
	(b) Sun, S; Fu, J. Bioorg. Med. Chem. Lett. 2018, 28, 3283. doi: 10.1016/j.bmcl.2018.09.016 pmid: 21631125
[31]	Schonherr, H.; Cernak, T. Angew. Chem., Int. Ed. 2013, 52, 12256. doi: 10.1002/anie.201303207
[32]	Ni, S.; Hribersek, M.; Baddigam, S. K.; Ingner, F. J. L.; Orthaber, A.; Gates, P. J.; Pilarski, L. T. Angew. Chem., Int. Ed. 2021, 60, 6660. doi: 10.1002/anie.v60.12
[33]	Yu, J.; Zhang, C.; Yang, X.; Su, W. Org. Biomol. Chem. 2019, 17, 4446. doi: 10.1039/C9OB00622B
[34]	(a) Pan, C.; Jin, H.; Liu, X.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 2933. doi: 10.1039/c3cc40709h
	(b) Yu, L.; Li, P.; Wang, L. Chem. Commun. 2013, 49, 2368. doi: 10.1039/c3cc40389k
	(c) Wang, C.; Wang, S.; Li, H.; Yan, J.; Chi, H.; Chen, X.; Zhang, Z. Org. Biomol. Chem. 2014, 12, 1721. doi: 10.1039/c3ob42171f
[35]	Su, W.; Yu, J.; Li, Z.; Jiang, Z. J. Org. Chem. 2011, 76, 9144. doi: 10.1021/jo2015533
[36]	Yu, J.; Li, Z.; Jia, K.; Jiang, Z.; Liu, M.; Su, W. Tetrahedron Lett. 2013, 54, 2006. doi: 10.1016/j.tetlet.2013.02.007
[37]	Ryu, J.; Kwak, J.; Shin, K.; Lee, D.; Chang, S. J. Am. Chem. Soc. 2013, 135, 12861. doi: 10.1021/ja406383h
[38]	(a) Hermann, G. N.; Becker, P.; Bolm, C. Angew. Chem., Int. Ed. 2016, 55, 3781. doi: 10.1002/anie.201511689
	(b) Lee, D.; Kim, Y.; Chang, S. J. Org. Chem. 2013, 78, 11102. doi: 10.1021/jo4019683
[39]	(a) Dubè, P.; Nathel, N. F. F.; Vetelino, M.; Couturier, M.; Aboussafy, C. L. E.; Pichette, S.; Jorgensen, M. L.; Hardink, M. Org. Lett. 2009, 11, 5622. doi: 10.1021/ol9023387
	(b) Bizet, V.; Buglioni, L.; Bolm, C. Angew. Chem., Int. Ed. 2014, 53, 5639. doi: 10.1002/anie.v53.22
	(c) Buglioni, L.; Bizet, V.; Bolm, C. Adv. Synth. Catal. 2014, 356, 2209. doi: 10.1002/adsc.v356.10
[40]	Hermann, G. N.; Bolm, C. ACS Catal. 2017, 7, 4592. doi: 10.1021/acscatal.7b00582
[41]	Cheng, H.; Hernández, J. G.; Bolm, C. Adv. Synth. Catal. 2018, 360, 1800. doi: 10.1002/adsc.v360.9
[42]	Yetra, S. R.; Shen, Z.; Wang, H.; Ackermann, L. Beilstein J. Org. Chem. 2018, 14, 1546. doi: 10.3762/bjoc.14.131
[43]	Li, L; Wang, G.-W. Tetrahedron 2018, 74, 4188. doi: 10.1016/j.tet.2018.06.003
[44]	Lu, X.; Bai, Y.; Qin, J.; Wang, N.; Wu, Y.; Zhong, F. ACS Sustainable Chem. Eng. 2021, 9, 1684. doi: 10.1021/acssuschemeng.0c07512
[45]	Hernandez, J. G.; Bolm, C. Chem. Commun. 2015, 51, 12582. doi: 10.1039/C5CC04423E
[46]	Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414. doi: 10.1021/ja802415h
[47]	Liu, Z.; Xu, H.; Wang, G.-W. Beilstein J. Org. Chem. 2018, 14, 430. doi: 10.3762/bjoc.14.31 pmid: 29520307
[48]	Pang, Y.; Ishiyama, T.; Kubota, K.; Ito, H. Chemistry 2019, 25, 4654.
[49]	(a) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890. doi: 10.1021/cr900206p
	(b) Xu, L.; Wang, G.; Zhang, S.; Wang, H.; Wang, L.; Liu, L.; Jiao, J.; Li, P. Tetrahedron 2017, 73, 7123. doi: 10.1016/j.tet.2017.11.005
[50]	(a) Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141. pmid: 16524288
	(b) Wang, G.-W.; Yuan, T. T. J. Org. Chem. 2010, 75, 476. doi: 10.1021/jo902139b pmid: 16524288
	(c) Zhang, S. Y.; He, G.; Zhao, Y.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313. doi: 10.1021/ja3023972 pmid: 16524288
[51]	Zhou, K.; Hao, H.-Y.; Mao, Y.-J.; Wu, Q.-Z.; Chen, L.; Wang, S.; Jin, W.; Xu, Z.-Y.; Lou, S.-J.; Xu, D.-Q. ACS Sustainable Chem. Eng. 2021, 9, 4433. doi: 10.1021/acssuschemeng.0c08201
[52]	Li, L; Wang, J. J.; Wang, G.-W. J. Org. Chem. 2016, 81, 5433. doi: 10.1021/acs.joc.6b00786
[53]	Hermann, G. N.; Jung, C. L.; Bolm, C. Green Chem. 2017, 19, 2520. doi: 10.1039/C7GC00499K
[54]	Schobel, J. H.; Elbers, P.; Truong, K. N.; Rissanen, K.; Bolm, C. Adv. Synth. Catal. 2021, 363, 1. doi: 10.1002/adsc.v363.1
[55]	Achar, T. K.; Mal, P. J. Org. Chem. 2015, 80, 666. doi: 10.1021/jo502464n
[56]	Achar, T. K.; Mal, P. Adv. Synth. Catal 2015, 357, 3977. doi: 10.1002/adsc.201500914
[57]	Hari, D. P.; Schroll, P.; Konig, B. J. Am. Chem. Soc. 2012, 134, 2958. doi: 10.1021/ja212099r
[58]	Kubota, K.; Pang, Y.; Miura, A.; Ito, H. Science 2019, 366, 1500. doi: 10.1126/science.aay8224 pmid: 31857482
[59]	Pang, Y.; Lee, J. W.; Kubota, K.; Ito, H. Angew. Chem., Int. Ed. 2020, 59, 22570. doi: 10.1002/anie.v59.50
[60]	Qin, J.; Zuo, H.; Ni, Y.; Yu, Q.; Zhong, F. ACS Sustainable Chem. Eng. 2020, 8, 12342. doi: 10.1021/acssuschemeng.0c03942
[61]	(a) Vásquez-Céspedes, S.; Ferry, A.; Candish, L.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 5772. doi: 10.1002/anie.201411997
	(b) Yi, S.; Li, M.; Mo, W.; Hu, X.; Hu, B.; Sun, N.; Jin, L.; Shen, Z. Tetrahedron Lett. 2016, 57, 1912. doi: 10.1016/j.tetlet.2016.03.073
[62]	Edson, de Oliveira Lima Filho; Malvestiti, I. ACS Omega 2020, 5, 33329. doi: 10.1021/acsomega.0c05131
[63]	(a) Exner, B.; Bayarmagnai, B.; Matheis, C.; Goossen, L. J. J. Fluorine Chem. 2017, 198, 89.
	(b) Jiang, H.; Yu, W.; Tang, X.; Li, J.; Wu, W. J. Org. Chem. 2017, 82, 9312. doi: 10.1021/acs.joc.7b01122
	(c) Wu, D.; Qiu, J.; Karmaker, P. G.; Yin, H.; Chen, F. X. J. Org. Chem. 2018, 83, 1576. doi: 10.1021/acs.joc.7b02850
[64]	Friščić, T.; Fábián, L. CrystEngComm 2009, 11, 743. doi: 10.1039/b822934c

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