Visible-light-induced and iron-catalyzed methylation of N-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles

Visible-light-induced and iron-catalyzed methylation of N-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles

Org. Biomol. Chem., 2017, Advance Article
DOI: 10.1039/C7OB00779E, Paper

Zuguang Xie, Pinhua Li, Yu Hu, Ning Xu, Lei Wang
An efficient synthesis of 3-ethyl-3-methyl oxindoles by visible-light promoted and iron-catalyzed difunctionalization of N-arylacrylamides with dimethyl sulphoxide was developed

Visible-light-induced and iron-catalyzed methylation of N-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles

Zuguang Xie,a  Pinhua Li,*a  Yu Hu,a  Ning Xua  and  Lei Wang*ab 

Author affiliations

*Corresponding authors

aDepartment of Chemistry, Huaibei Normal University, Huaibei, P. R. China
E-mail: pphuali@126.com, leiwang@chnu.edu.cn
Fax: +86-561-3090-518
Tel: +86-561-3802-069

bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China

Abstract

A visible-light-induced and iron-catalyzed methylation of arylacrylamides by dimethyl sulphoxide (DMSO) is achieved, leading to 3-ethyl-3-methyl indolin-2-ones in high yields. This reaction tolerates a series of functional groups, such as methoxy, trifluoromethyl, cyano, nitro, acetyl and ethyloxy carbonyl groups. The visible-light promoted radical methylation and arylation of the alkenyl group are involved in this reaction.

 

 

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