Department of Chemistry, University of California, Irvine, 4403 Natural Sciences 1, Irvine, CA, 92697, USA.
Angew Chem Int Ed Engl. 2017 Sep 11;56(38):11589-11593. doi: 10.1002/anie.201705859. Epub 2017 Aug 10.
We have developed a strategy to transform olefins into homoallylic nitriles through a mechanism that combines copper catalysis with alkyl nitrile radicals. The radicals are easily generated from alkyl nitriles in the presence of the mild oxidant di-tert-butyl peroxide. This cross-dehydrogenative coupling between simple olefins and alkylnitriles bears advantages over the conventional use of halides and toxic cyanide reagents. With this method, we showcase the facile synthesis of a flavoring agent, a natural product, and a polymer precursor from simple olefins.
我们开发了一种通过铜催化与烷基腈自由基相结合的机制将烯烃转化为偕亚丙基腈的策略。在温和氧化剂二叔丁基过氧化物的存在下，自由基很容易从烷基腈中生成。这种简单烯烃和烷基腈之间的交叉脱氢偶联反应优于传统的卤化物和有毒氰化物试剂的使用。使用这种方法，我们从简单烯烃中轻松合成了一种调味剂、一种天然产物和一种聚合物前体。
