Issue 7, 2025

Visible-light-induced radical-cascade alkylation/cyclization of acrylamides: access to 3,3-dialkylated oxindoles

Abstract

A visible-light-induced deoxygenative alkylation/cyclization of acrylamides with alcohols activated by CS2 has been developed by using xanthate salts as alkyl radical precursors in the presence of tricyclohexylphosphine. It proceeds through a tandem radical addition/cyclization process, and this protocol provides a reliable and practical approach to building the skeleton of 3,3-disubstituted oxindoles in moderate to good yields. Notable features of this reaction include readily available starting reagents, broad substrate scope and mild reaction conditions.

Graphical abstract: Visible-light-induced radical-cascade alkylation/cyclization of acrylamides: access to 3,3-dialkylated oxindoles

Supplementary files

Article information

Article type
Paper
Submitted
29 Oct 2024
Accepted
31 Dec 2024
First published
02 Ian 2025

Org. Biomol. Chem., 2025,23, 1653-1661

Visible-light-induced radical-cascade alkylation/cyclization of acrylamides: access to 3,3-dialkylated oxindoles

P. Yang, L. Wang, M. Yan, J. Yuan, Y. Xiao, L. Yang, X. Xu and L. Qu, Org. Biomol. Chem., 2025, 23, 1653 DOI: 10.1039/D4OB01739K

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