Photoredox nickel-catalyzed radical cyclization of -arylacrylamides with alkyl bromides.

Org Biomol Chem

College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.

Published: February 2025

3,3-Disubstituted oxindoles constitute a significant class of biologically active molecules, often found in a wide range of bioactive compounds. In this work, we present a photoredox nickel-catalyzed intermolecular cyclization between -arylacrylamides and readily accessible alkyl bromides, which affords a diverse range of 3,3-disubstituted oxindoles in moderate to high yields. Our mechanistic studies reveal that the reduction of alkyl bromides single-electron transfer from a reactive Ni(I) species is a critical step in driving this radical cascade transformation. This approach offers several advantages, including mild reaction conditions, broad functional group tolerance, and a simple workup procedure.

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http://dx.doi.org/10.1039/d5ob00078eDOI Listing

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