数字农科院2.0

NHC Precursor Catalyzed C3-Chloromethylation of Oxindole with Dichloromethane as C1 Synthon

文献类型： 外文期刊

作者： Liang, Lijuan;Loh, Teck-Peng;Li, Yaojie;Hu, Rong-Bin;Zhang, Yu;Li, Ruoqi;Zhang, Hao;Chen, Peng;Jia, Zhenhua

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期刊名称： ORGANIC LETTERS

ISSN： 1523-7060

年卷期： 2025 年

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收录情况： SCIE（2025版）

摘要： The construction of sterically hindered all-carbon alpha-chloromethyl quaternary centers remains a major synthetic challenge due to both steric congestion and limited efficient methods. Herein, we report a mild and efficient protocol for the chloromethylation of oxindoles using dichloromethane (DCM) as a C1 synthon, mediated by an NHC precursor. This reaction proceeded under mild conditions with broad substrate scope, high chemoselectivity, and good to excellent yields across over 30 examples. Preliminary mechanistic studies suggested a unique pathway distinct from that of conventional NHC catalysis. The method demonstrated excellent scalability and offered a versatile and green approach to access alpha-chloromethyl quaternary centers, providing valuable intermediates for further transformations in pharmaceutical and organic synthesis.

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