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Access to Branched Allylarenes via Rhodium(III)-Catalyzed C–H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate

Shang‐Shi Zhang, Yi‐Chuan Zheng, Zi-Wu Zhang, Shaoyong Chen, Hui Xie, Bing Shu, Jia‐Lin Song, Yanzhi Liu, Yao‐Fu Zeng, Luyong Zhang

2021Organic Letters32 citationsDOI

Abstract

A rhodium(III)-catalyzed C–H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

Topics & Concepts

ChemistryRhodiumCatalysisCarbonateMedicinal chemistryStereochemistryOrganic chemistryCombinatorial chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions
Access to Branched Allylarenes via Rhodium(III)-Catalyzed C–H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate | Litcius