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光诱导钯催化的烯丙基碳氢键直接磺酰化反应

Photoinduced Pd-Catalyzed Direct Sulfonylation of Allylic C-H Bonds.

作者信息

Mukherjee Kallol, Cheung Kelvin Pak Shing, Gevorgyan Vladimir

机构信息

Department of Chemistry and Biochemistry, The University of Texas at Dallas, 800 West Campbell Road, Richardson, Texas, 75080-3021, United States.

出版信息

Angew Chem Int Ed Engl. 2025 Jan 2;64(1):e202413646. doi: 10.1002/anie.202413646. Epub 2024 Nov 7.

Abstract

Allylic sulfones are valuable motifs due to their medicinal and biological significance and their versatile chemical reactivities. While direct allylic C-H sulfonylation represents a straightforward and desirable approach, these methods are primarily restricted to terminal alkenes, leaving the engagement of the internal counterparts a formidable challenge. Herein we report a photocatalytic approach that accommodates both cyclic and acyclic internal alkenes with diverse substitution patterns and electronic properties. Importantly, the obtained allylic sulfones can be readily diversified into a wide range of products, thus enabling formal alkene transposition and all-carbon quaternary center formation through the sequential C-H functionalization.

摘要

烯丙基砜由于其医学和生物学意义以及多样的化学反应活性而成为有价值的结构单元。虽然直接的烯丙基C-H砜基化是一种直接且理想的方法,但这些方法主要限于末端烯烃,使内部烯烃的反应成为一项艰巨的挑战。在此,我们报道了一种光催化方法,该方法适用于具有不同取代模式和电子性质的环状和非环状内部烯烃。重要的是,所得到的烯丙基砜可以很容易地转化为多种产物,从而通过连续的C-H官能化实现形式上的烯烃换位和全碳季碳中心的形成。

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