Issue 11, 2014

1,2-Alkylarylation of activated alkenes with dual C–H bonds of arenes and alkyl halides toward polyhalo-substituted oxindoles

Abstract

We describe here a new visible light facilitated radical strategy for 1,2-alkylarylation of activated alkenes with a C(sp2)–H bond of arenes and a C(sp3)–H bond of alkyl halides. This method achieves selective scission of the C(sp3)–H bond adjacent to halide atoms leading to a halo-substituted alkyl radical, and provides a new synthetic utilization of aryl halides toward polyhalo-substituted oxindoles in good to excellent yields. Moreover, the concise transformation of the products, polyhalo-substituted oxindoles, into vinyl halides and alkynyl halides was also illustrated.

Graphical abstract: 1,2-Alkylarylation of activated alkenes with dual C–H bonds of arenes and alkyl halides toward polyhalo-substituted oxindoles

Supplementary files

Article information

Article type
Research Article
Submitted
19 Sep 2014
Accepted
06 Nov 2014
First published
06 Nov 2014

Org. Chem. Front., 2014,1, 1289-1294

Author version available

1,2-Alkylarylation of activated alkenes with dual C–H bonds of arenes and alkyl halides toward polyhalo-substituted oxindoles

Y. Liu, J. Zhang, R. Song and J. Li, Org. Chem. Front., 2014, 1, 1289 DOI: 10.1039/C4QO00251B

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