Issue 42, 2024

Construction of contiguous quaternary carbon centers enabled by dearomatization of phenols with 3-bromooxindoles

Abstract

A transition metal-free and oxidation-free dearomatization of phenols through conjugate addition to in situ generated indol-2-one from 3-bromooxindole is detailed in this report. This methodology offers an effective approach for the synthesis of a range of 3-substituted oxindoles containing contiguous quaternary carbon centers (CQCCs) with yields of up to 99%. The reaction is characterized by mild conditions, exceptional efficiency, environmental compatibility, favorable functional group tolerance, and scalability to large-scale production.

Graphical abstract: Construction of contiguous quaternary carbon centers enabled by dearomatization of phenols with 3-bromooxindoles

Supplementary files

Article information

Article type
Communication
Submitted
12 Jul 2024
Accepted
20 Sep 2024
First published
23 Sep 2024

Org. Biomol. Chem., 2024,22, 8413-8417

Construction of contiguous quaternary carbon centers enabled by dearomatization of phenols with 3-bromooxindoles

H. Li, X. Wang, M. Chang, M. Wu, X. Yuan, X. Hui, H. Wei, J. Xi and W. Xie, Org. Biomol. Chem., 2024, 22, 8413 DOI: 10.1039/D4OB01163E

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