Recent Progress in C—H Bond Activation Reaction with Vinylene Carbonate

doi:10.6023/cjoc202302009

Abstract

Transition metal-catalyzed directed C—H bond activation reactions have emerged as a simple and powerful strategy for the construction of multifarious organic molecules due to their high atom-economy and regioselectivity. Among various coupling reagents, vinylene carbonate as a novel and multifunctional coupling reagent has been extensively explored in the transition-metal-catalyzed C—H bond functionalization. In this paper, the recent progress on the application of vinylidene carbonate in C—H bond activation reactions is summarized and the prospect of vinylidene carbonate is discussed.

Key words: vinylene carbonate, transition metal-catalysis, C—H bond activation

Cite this article

Xiaoyang Gao, Ruirui Zhai, Xun Chen, Shuojin Wang. Recent Progress in C—H Bond Activation Reaction with Vinylene Carbonate[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3119-3134.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 38

Scheme 1. Transition metal-catalyzed C—H bond activation reaction with vinylene carbonate

Scheme 2. Rh(III)-catalyzed [4+2] annulation of benzamides with vinylene carbonate

Scheme 3. Proposed reaction mechanism for the Rh(III)- catalyzed [4+2] annulation of benzamides with vinylene carbonate

Scheme 4. Rh(III)-catalyzed [3+2] annulation of 3-hydroxy- benzamides with vinylene carbonate

Scheme 5. Co(III)-catalyzed [4+2] cyclization of benzamide with vinylene carbonate

Scheme 6. Total synthesis of 8-oxopseudopalmatine and oxopalmatine

Scheme 7. Rate-determining step of annulation of benzamides and vinylene carbonate

Scheme 8. Rh(III)- and Ru(II)-catalyzed [4+2] cyclization of 2-phenylquinazolinone with vinylene carbonate

Scheme 9. Ru(II)-catalyzed [4+2] cyclization of 2-phenyl- quinazolinone with vinylene carbonate

Scheme 10. Ru(II)-catalyzed quinazolinone-directed (hetero)- arene or alkene C—H bond [4+2] cyclization with vinylene carbonate

Scheme 11. Total synthesis of rutaecarpine natural products

Scheme 12. Rh(III)-catalyzed [4+2] cyclization of N-arylmeth- animines with vinylene carbonate

Scheme 13. Proposed reaction mechanism for the Rh(III)-cata- lyzed [4+2] annulation of N-arylmethanimines with vinylene carbonate

Scheme 14. Rh(III)-catalyzed [4+2] cyclization of imines and vinylene carbonate

Scheme 15. Mn(I)-catalyzed annulation of imines with vinylene carbonate

Scheme 16. Rh(III)-catalyzed [4+2] annulation of benzoic acid with vinylene carbonate

Scheme 17. Rh(III)-catalyzed [4+2] annulation of sulfonyl benzamide and vinylene carbonate

Scheme 18. Rh(III)-catalyzed annulation of imidazopyridine with vinylene carbonate

Scheme 19. Co(III)-catalyzed [4+2] annulation of imidazopyri- dine with vinylene carbonate

Scheme 20. Rh(III)-catalyzed [4+2] annulation of 3-aryliso- xazoles with vinylene carbonate

Scheme 21. Rh(III)-catalyzed [4+2] annulation of N-arylin- dazolones with vinylene carbonate

Scheme 22. Rh(III)-catalyzed [4+2] annulation of N-arylpyra- zolidinone with vinylene carbonate

Scheme 23. Rh(III)-catalyzed [4+2] annulation of enaminones with vinylene carbonate

Scheme 24. Ru(II)-catalyzed [3+2] cyclization of N-phenyl- pyranamide with vinylene carbonate

Scheme 25. Rh(III)-catalyzed [5+1] annulation of 2-pyrrolyl- aniline with vinylene carbonate

Scheme 26. Rh(III)-catalyzed [5+1] annulation of 2-indolylaniline with vinylene carbonate

Scheme 27. Rh(III)-catalyzed [4+1] or [4+2] annulation of azobenzenes with vinylene carbonate

Scheme 28. Rh(III)-catalyzed [4+1] annulation of azobenzenes with vinylene carbonate

Scheme 29. Rh(III)-catalyzed [5+1] annulation of imines with vinylene carbonate

Scheme 30. Rh(III)-catalyzed [3+2+1] annulation of phenylamine with vinylene carbonate

Scheme 31. Synthetic applications of benzoquinoline

Scheme 32. Rh(III)-catalyzed cascade annulation of azobenzenes with vinylene carbonate

Scheme 33. Proposed reaction mechanism for the Rh(III)-catalyzed cascade annulation of azobenzenes with vinylene carbonate

Scheme 34. Rh(III)-catalyzed acylmethylation of N-arylpyra- zole with vinylene carbonate

Scheme 35. Proposed reaction mechanism for Rh(III)-catalyzed acylmethylation of N-arylpyrazole with vinylene carbonate

Scheme 36. Rh(III)-catalyzed acylmethylation of N-pyrimi- dylindol and N-pyrimidylindoline with vinylene carbonate

Scheme 37. Rh(III)-catalyzed acylmethylation of N-pyrimi- dylindol with vinylene carbonate

Scheme 38. Ru(II)-catalyzed acylmethylation and acetalization of N-pyrimidylindoline with vinylene carbonate

References 49

[1]	For selected review, see (a) He Y.; Huang, Z.; Wu, K.; Ma, J.; Zhou, Y. G.; Yu, Z. Chem. Soc. Rev. 2022, 51, 2759. doi: 10.1039/D1CS00895A
	(b) Murali K.; Machado L. A.; Carvalho R. L.; Pedrosa L. F.; Mukherjee R.; Da Silva Júnior E. N.; Maiti D. Chem.-Eur. J. 2021, 27, 12453. doi: 10.1002/chem.v27.49
	(c) Liu B.; Yang L.; Li P.; Wang F.; Li X. Org. Chem. Front. 2021, 8, 1085. doi: 10.1039/D0QO01159B
[2]	Kumrua B.; Bicak N. RSC Adv. 2015, 5, 30936. doi: 10.1039/C5RA02783G
[3]	Fasulo F.; Munoz-Garcia A. B.; Massaro A.; Crescenzi O.; Huang C.; Pavone M. J. Mater. Chem. A 2023, 11, 5660. doi: 10.1039/D2TA08772C
[4]	Taffin C.; Kreutler G.; Bourgeois D.; Clotb E.; Périgauda C. New J. Chem. 2010, 34, 517. doi: 10.1039/b9nj00536f
[5]	Ghosh K.; Nishii Y.; Miura M. ACS Catal. 2019, 9, 11455. doi: 10.1021/acscatal.9b04254
[6]	(a) Bettica P.; Squassante L.; Groeger J. A.; Gennery B.; Winsky- Sommerer R.; Dijk D.-J. Neuropsychopharmacology 2012, 37, 1224. doi: 10.1038/npp.2011.310 pmid: 2153208
	(b) Halfpenny P. R.; Horwell D. C.; Hughes J.; Hunter J. C.; Rees D. C. J. Med. Chem. 1990, 33, 286. pmid: 2153208
[7]	Kitano J.; Nishii Y.; Miura M. Org. Lett. 2022, 24, 5679. doi: 10.1021/acs.orglett.2c02030
[8]	Li X.; Huang T.; Song Y.; Qi Y.; Li L.; Li Y.; Xiao Q.; Zhang Y. Org. Lett. 2020, 22, 5925. doi: 10.1021/acs.orglett.0c02016
[9]	Shen B.; Liu S.; Zhu L.; Zhong K.; Liu F.; Chen H.; Bai R.; Lan Y. Organometallics 2020, 39, 2813. doi: 10.1021/acs.organomet.0c00248
[10]	(a) Khan I.; Ibrar A.; Abbas N.; Saeed A. Eur. J. Med. Chem. 2014, 76, 193. doi: 10.1016/j.ejmech.2014.02.005 pmid: 30908968
	(b) Rakesh K. P.; Kumara H. K.; Manukumar H. M.; Gowda D. C. Bioorg. Chem. 2019, 87, 252. doi: S0045-2068(19)30088-4 pmid: 30908968
[11]	(a) Sun J.; Tan Q.; Yang W.; Liu B.; Xu B. Adv. Synth. Catal. 2014, 356, 388. doi: 10.1002/adsc.v356.2/3
	(b) Chen J.; Natte K.; Spannenberg A.; Neumann H.; Langer P.; Beller M.; Wu X.-F. Angew. Chem. 2014, 126, 7709. doi: 10.1002/ange.201402779
	(c) Liang D.; He Y.; Zhu Q. Org. Lett. 2014, 16, 2748. doi: 10.1021/ol501070g
[12]	Wang L.; Jiang K.-C.; Zhang N.; Zhang Z.-H. Asian J. Org. Chem. 2021, 10, 1671. doi: 10.1002/ajoc.v10.7
[13]	Wang Z.-H.; Wang H.; Wang H.; Li L.; Zhou M.-D. Org. Lett. 2021, 23, 995. doi: 10.1021/acs.orglett.0c04200
[14]	Chen Y.; Huang X.; Xu Y.; Li J.; Lai R.; Guan M.; Wu Y. Synlett 2021, 32, 1963. doi: 10.1055/a-1608-5381
[15]	Nan J.; Huang G.; Hu Y.; Wang B. Chin. J. Org. Chem. 2023, 43, 1537. (in Chinese) doi: 10.6023/cjoc202210003
	(南江, 黄冠杰, 胡岩, 王波, 有机化学, 2023, 43, 1537.) doi: 10.6023/cjoc202210003
[16]	Shang X.-F.; Morris-Natschke S. L.; Liu Y.-Q.; Guo X.; Xu X.-S.; Goto M.; Li J.-C.; Yang G.-Z.; Lee K.-H. Med. Res. Rev. 2018, 38, 775. doi: 10.1002/med.2018.38.issue-3
[17]	Hu Y.; Nan J.; Yin J.; Huang G.; Ren X.; Ma Y. Org. Lett. 2021, 23, 8527. doi: 10.1021/acs.orglett.1c03231
[18]	Zhao X.; Pang H.; Huang D.; Liu G.; Hu J.; Xiang Y. Angew. Chem., Int. Ed. 2022, 61, e202208833. doi: 10.1002/anie.v61.41
[19]	Huang X.; Xu Y.; Li J.; Lai R.; Luo Y.; Wang Q.; Yang Z.; Wu Y. Chin. Chem. Lett. 2021, 32, 3518. doi: 10.1016/j.cclet.2021.04.058
[20]	(a) Hu Y.; Wang C. ChemCatChem 2019, 11, 1167. doi: 10.1002/cctc.v11.4
	(b) Hu Y.; Zhou B.; Chen H.; Wang C. Angew. Chem., Int. Ed. 2018, 57, 12071. doi: 10.1002/anie.v57.37
	(c) Liu T.; Hu Y.; Yang Y.; Wang C. CCS Chem. 2021, 3, 749. doi: 10.31635/ccschem.020.202000206
[21]	Li Y.; Wang H.; Li Y.; Li Y.; Sun Y.; Xia C.; Li Y. J. Org. Chem. 2021, 86, 18204. doi: 10.1021/acs.joc.1c02473
[22]	(a) Saeed A. Eur. J. Med. Chem. 2016, 116, 290. doi: 10.1016/j.ejmech.2016.03.025
	(b) Saddiqa A.; Usman M.; Cakmak O. Turk. J. Chem. 2017, 41, 153. doi: 10.3906/kim-1604-66
[23]	Mihara G.; Ghosh K.; Nishii Y.; Miura M. Org. Lett. 2020, 22, 5706. doi: 10.1021/acs.orglett.0c02112 pmid: 32638595
[24]	Wang L.; Shao Y.; Chen F.; Qian P.-C.; Cheng J. Chin. J. Org. Chem. 2022, 42, 242. (in Chinese) doi: 10.6023/cjoc202106023
	(王璐, 邵莺, 陈帆, 钱鹏程, 成江, 有机化学, 2022, 42, 242.) doi: 10.6023/cjoc202106023
[25]	Ghosh K.; Nishii Y.; Miura M. ACS Catal. 2019, 9, 11455. doi: 10.1021/acscatal.9b04254
[26]	Ghosh K.; Nishii Y.; Miura M. Org. Lett. 2020, 22, 3547. doi: 10.1021/acs.orglett.0c00975
[27]	Liu M.; Sui X.; Wen J.; Li Q.; Liu X.; Wang X.; Wang X.; Yan K. Eur. J. Org. Chem. 2023, 43, 153.
[28]	Kumar P.; Kapur M. Chem. Commun. 2022, 58, 4476. doi: 10.1039/D2CC01048H
[29]	(a) Han Y. T.; Jung J.-W.; Kim N.-J. Curr. Org. Chem. 2017, 21, 1265. doi: 10.2174/1385272821666170221150901
	(b) Szumilak M.; Stanczak A. Molecules 2019, 24, 2271. doi: 10.3390/molecules24122271
[30]	Kim S.; Choi S. B.; Kang J. Y.; An W.; Lee S. H.; Oh H.; Ghosh P.; Mishra N. K.; Kim I. S. Asian J. Org. Chem. 2021, 10, 1. doi: 10.1002/ajoc.v10.1
[31]	(a) Zhang G.; Miao J.; Zhao Y.; Ge H. Angew. Chem., Int. Ed. 2012, 51, 8318. doi: 10.1002/anie.v51.33
	(b) Lan C.; Tian Z.; Liang X.; Gao M.; Liu W.; An Y.; Fu W.; Jiao G.; Xiao J.; Xu B. Adv. Synth. Catal. 2017, 359, 3735. doi: 10.1002/adsc.v359.21
[32]	Huang G.; Yu J.-T.; Pan C. Eur. J. Org. Chem. 2022, 2022, e202200279.
[33]	Zhang S.; Hu S.; Wang K.; Yang Z.; Liu H.; Wang J. Adv. Synth. Catal. 2023, 365, 238. doi: 10.1002/adsc.v365.2
[34]	(a) Singh R. B.; Mahanta S.; Guchhait N.; Photochem J. J. Photochem. Photobiol., B 2008, 91, 1. doi: 10.1016/j.jphotobiol.2007.12.006
	(b) Jin Q.; Wang F.; Chen S.; Zhou L.; Jiang H.; Zhang L.; Liu M. Chem. Asian J. 2020, 15, 319. doi: 10.1002/asia.v15.2
[35]	Liu M.; Yan K.; Wen J.; Liu W.; Wang M.; Wang L.; Wang X. Adv. Synth. Catal. 2022, 364, 512. doi: 10.1002/adsc.v364.3
[36]	(a) Meng Y.; Yu B.; Huang H.; Peng Y.; Li E.; Yao Y.; Song C.; Yu W.; Zhu K.; Wang K.; Yi D.; Du J.; Chang J. Med. Chem. 2021, 64, 925. doi: 10.1021/acs.jmedchem.0c02005 pmid: 33215494
	(b) Feng X.; Liao D.; Liu D.; Ping A.; Li Z.; Bian J. J. Med. Chem. 2020, 63, 15115. doi: 10.1021/acs.jmedchem.0c00925 pmid: 33215494
[37]	Yu Y.; Wang Y.; Li B.; Tan Y.; Zhao H.; Li Z.; Zhang C.; Ma W. Adv. Synth. Catal. 2022, 364, 838. doi: 10.1002/adsc.v364.4
[38]	Nan J.; Ma Q.; Yin J.; Liang C.; Tian L.; Ma Y. Org. Chem. Front. 2021, 8, 1764. doi: 10.1039/D1QO00040C
[39]	Hu F.-P.; Zhang X.-G.; Wang M.; Wang H.-S.; Huang G.-S. Chem. Commun. 2021, 57, 11980. doi: 10.1039/D1CC05059A
[40]	Park M. S.; Moon K.; Oh H.; Lee J. Y.; Ghosh P.; Kang J. Y.; Park J. S.; Mishra N. K.; Kim I. S. Org. Lett. 2021, 23, 5518. doi: 10.1021/acs.orglett.1c01866 pmid: 34228466
[41]	Zhang W.-J.; Li C.; Wang B.-C.; Gao H.; Li H.-J. Chin. J. Org. Chem. 2022, 42, 172. (in Chinese) doi: 10.6023/cjoc202107038
	(张文杰, 李超, 王博超, 高慧, 李洪基, 有机化学, 2022, 42, 172.) doi: 10.6023/cjoc202107038
[42]	Wang C.; Fan X.; Chen F.; Qian P.-C.; Cheng J. Chem. Commun. 2021, 57, 3929. doi: 10.1039/D1CC00882J
[43]	Nan J.; Yin J.; Gong X.; Hu Y.; Ma Y. Org. Lett. 2021, 23, 8910. doi: 10.1021/acs.orglett.1c03404
[44]	(a) Sreedevi R.; Saranya S.; Rohit K. R.; Anilkumar G. Adv. Synth. Catal. 2019, 361, 2236. doi: 10.1002/adsc.v361.10
	(b) Hashem H.; ElBakri Y. Arabian J. Chem. 2021, 14, 103418. doi: 10.1016/j.arabjc.2021.103418
[45]	Hu W.; Pi C.; Hu D.; Han X.; Wu Y.; Cui X. Org. Lett. 2022, 24, 2613. doi: 10.1021/acs.orglett.2c00580
[46]	Kato M.; Ghosh K.; Nishii Y.; Miura M. Chem. Commun. 2021, 57, 8280. doi: 10.1039/D1CC03362J
[47]	Hu W.; Wang X.; Yu X.; Zhu X.; Hao X.-Q.; Song M.-P. Asian J. Org. Chem. 2021, 10, 2557. doi: 10.1002/ajoc.v10.10
[48]	Li B.-S.; Guo H.-X.; Sun W.; Sun M. Tetrahedron Lett. 2022, 99, 153854. doi: 10.1016/j.tetlet.2022.153854
[49]	Liu M.; Yan K.; Wen J.; Shang W.; Sui X.; Wang X. Adv. Synth. Catal. 2022, 364, 1580. doi: 10.1002/adsc.v364.9

碳酸亚乙烯酯参与C—H键活化反应的研究进展