镍催化环丁酮肟酯与芳基锌试剂的Negishi偶联反应

doi:10.6023/cjoc201911016

摘要/Abstract

发展了一种镍催化环丁酮肟酯和芳基锌试剂之间Negishi偶联的方法.镍既作为亚胺自由基的引发剂，也作为芳基锌试剂与烷基自由基偶联反应的催化剂在反应中起作用.本方法可避免使用剧毒的氰化物，且具有很广的底物适应性和官能团兼容性，因此可能是一种具有潜在吸引力的高效合成烷基腈类化合物的新策略.初步的机理研究显示，该反应极可能经历自由基历程.

关键词: Negishi偶联, 镍, 环丁酮肟酯, 芳基锌试剂

A nickel-catalyzed Negishi coupling of cyclobutanone oxime esters with aryl zinc reagents has been developed, in which nickel serves both as an initiator for imine radicals and a catalyst for the coupling of aryl zinc reagents with oxime esters. The protocol can avoid the use of poisonous cyanide and has broad substrate scope as well as good functional group compatibility. Therefore, this method provides an attractive strategy for the synthesis of valuable nitriles. Preliminary mechanistic studies indicate that a radical pathway is involved in the product formation.

Key words: Negishi coupling, nickel, cyclobutanone oxime esters, aryl zinc reagents

引用此文

帅斌, 李兆明, 裘晖, 方萍, 梅天胜. 镍催化环丁酮肟酯与芳基锌试剂的Negishi偶联反应[J]. 有机化学, 2020, 40(3): 651-662.

Shuai Bin, Li Zhao-Ming, Qiu Hui, Fang Ping, Mei Tian-Sheng. Nickel-Catalyzed Negishi Coupling of Cyclobutanone Oxime Esters with Aryl Zinc Reagents[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 651-662.

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