Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry , Fujian Institute of Research on the Structure of Matter, Center for Excellence in Molecular Synthesis, Chinese Academy of Sciences , 155 Yangqiao Road West , Fuzhou , Fujian 350002 , P. R. China.
University of Chinese Academy of Sciences , Beijing , 100049 , P. R. China.
Org Lett. 2018 Jun 1;20(11):3202-3205. doi: 10.1021/acs.orglett.8b01043. Epub 2018 May 22.
This paper reports a new method for the generation of substituted 1,3-enynes, whose synthesis by other methods could be a challenge. The dehydrative decarboxylative cascade coupling reaction of propargyl alcohol with alkyl peroxides is enabled by an iron catalyst and alkylating reagents. Primary, secondary, and tertiary alkyl groups can be introduced into 1,3-enynes, affording various substituted 1,3-enynes in moderate to good yields. Mechanistic studies suggest the involvement of a radical-polar crossover pathway.
本文报道了一种生成取代 1,3-烯炔的新方法，其他方法的合成可能具有挑战性。通过铁催化剂和烷基化试剂，实现了丙炔醇与过氧烷基化合物的脱羧脱水级联偶联反应。伯、仲和叔烷基可以引入 1,3-烯炔中，以中等至良好的收率得到各种取代的 1,3-烯炔。机理研究表明该反应涉及自由基-极性交叉途径。
