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可见光照驱动的亚胺基自由基介导的肟酯 C-C 单键断裂/自由基加成级联反应。

A Visible-Light-Driven Iminyl Radical-Mediated C-C Single Bond Cleavage/Radical Addition Cascade of Oxime Esters.

机构信息

CCNU-uOttawa Joint Research Centre, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Key Laboratory of Pesticides & Chemical Biology Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, China.

出版信息

Angew Chem Int Ed Engl. 2018 Jan 15;57(3):738-743. doi: 10.1002/anie.201710618. Epub 2017 Dec 18.

DOI:10.1002/anie.201710618
PMID:29214705
Abstract

A room-temperature, visible-light-driven N-centered iminyl radical-mediated and redox-neutral C-C single bond cleavage/radical addition cascade reaction of oxime esters and unsaturated systems has been accomplished. The strategy tolerates a wide range of O-acyl oximes and unsaturated systems, such as alkenes, silyl enol ethers, alkynes, and isonitrile, enabling highly selective formation of various chemical bonds. This method thus provides an efficient approach to various diversely substituted cyano-containing alkenes, ketones, carbocycles, and heterocycles.

摘要

已实现了在室温、可见光驱动下,通过 N 中心亚胺基自由基介导和氧化还原中性 C-C 单键断裂/自由基加成级联反应,将肟酯和不饱和体系转化为各种含氰基的取代烯烃、酮、碳环和杂环化合物。该策略具有广泛的 O-酰基肟和不饱和体系(如烯烃、硅基烯醇醚、炔烃和异腈)耐受性,能够高度选择性地形成各种化学键。因此,该方法为各种取代的含氰基烯烃、酮、碳环和杂环化合物的合成提供了一种有效途径。

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