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Updated: Jun 11, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Construction of contiguous quaternary carbon centers enabled by dearomatization of phenols with 3-bromooxindoles
Hui Li1, Xi Wang1, Minhang Chang1
1Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, 22 Xinong Road, Yangling, 712100, Shaanxi, China. xiewq@nawafu.edu.cn.
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.
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