Copper ferrite catalyst for direct arylation of acidic C-H bonds in azoles with aryl aldehydes

Cuong Vu Minh, Anh Nguyen Thai, Nam Phan Thanh Son, Tung Nguyen Thanh

Abstract


Coupling reagents toward direct arylation of C2-H bonds in aryl azoles are often limited to aryl halides. Herein we report a functionalization of the acidic sp2 C-H bonds in benzothiazoles with benzaldehyde derivatives. Reactions proceeded in the presence of commercially ready CuFe2O4 catalyst. Scope of functional groups included chloro, nitro, cyano, and ester groups.

Keywords


copper ferrite; arylation; heterogeneous

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References


L. Ackermann, R. Vicente, in: L. Ackermann (Ed.), Modern Arylation Methods, Wiley-VCH: Weinheim, Germany, 2009, p. 311-333.

N.S. Gobalasingham, B.C. Thompson, Prog. Polym. Sci. 83 (2018) 135-201. https://doi.org/10.1016/j.progpolymsci.2018.06.002

S. Caille, S. Cui, M.M. Faul, S.M. Mennen, J.S. Tedrow, S.D. Walker, J. Org. Chem. 84 (2019) 4583-4603. https://doi.org/10.1021/acs.joc.9b00735

O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 42 (2009) 1074-1086. https://doi.org/10.1021/ar9000058

J. Huang, J. Chan, Y. Chen, C.J. Borths, K.D. Baucom, R.D. Larsen, M.M. Faul, J. Am. Chem. Soc. 132 (2010) 3674-3675. https://doi.org/10.1021/ja100354j

F. Gao, B.-S. Kim, P.J. Walsh, Chem. Commun. 50 (2014) 10661-10664. https://doi.org/10.1039/C4CC05307A

T. Piou, Y. Slutskyy, N.J. Kevin, Z. Sun, D. Xiao, J. Kong, Org. Lett. 23 (2021) 1996-2001. https://doi.org/10.1021/acs.orglett.1c00100

S. Liu, R. Chen, X. Gao, H. Yang, G. Deng, C.-J. Li, Green Chem. 14 (2012) 1577-1580. https://doi.org/ 10.1039/C2GC35457H

S.D. Doan, K.D. Nguyen, T.T. Nguyen, N.T.S. Phan, RSC Adv. 7 (2017) 1423-1431. https://doi.org/10.1039/ C6RA24716D

D.B. Eremin, V.P. Ananikov, Coord. Chem. Rev. 346 (2017) 2-19. https://doi.org/10.1016/j.ccr.2016.12.021

S. Vásquez-Céspedes, K.M. Chepiga, N. Möller, A.H. Schäfer, F. Glorius, ACS Catal. 6 (2016) 5954-5961. https://doi.org/10.1021/acscatal.6b01288

S. Vásquez-Céspedes, M. Holtkamp, U. Karst, F. Glorius, Synlett 28 (2017) 2759-2764. https://doi.org/10.1055/s-0036-1589007




DOI: https://doi.org/10.51316/jca.2021.070

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