Organocatalytic Three-Component 1,2-Cyanoalkylacylation of Alkenes via Radical Relay

作者：Yu Gao, Yusheng Quan, Zhenjiang Li, Luoyu Gao, Zhihao Zhang, Xin Zou, Rui Yan, Yuanyuan Qu, Kai Guo · 发表于：Organic Letters · 年份：2020 · DOI：10.1021/acs.orglett.0c03907 · 被引用次数：59 · 研究领域：N-Heterocyclic Carbenes in Organic and Inorganic Chemistry、Catalytic C–H Functionalization Methods、Catalytic Cross-Coupling Reactions

Here, we report an unprecedented regioselective, intermolecular 1,2-cyanoalkylacylation of feedstock alkenes with readily available oxime esters and aldehydes by N -heterocyclic carbene (NHC) organocatalysis. The crux of this success is the exquisite control over the radical relay process by an NHC organocatalyst. This protocol offers a general platform for diversity-oriented synthesis of valuable ketonitriles under mild, transition-metal-free, and redox-neutral conditions and highlights its potential in the late-stage functionalization of pharmaceutical architectures and natural products.