银介导的与碳亲核试剂的巴纳特串联反应
Silver Mediated Banert Cascade with Carbon Nucleophiles.
作者信息
Alexander Juliana R, Kevorkian Paul V, Topczewski Joseph J
机构信息
Department of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.
出版信息
Org Lett. 2021 Apr 16;23(8):3227-3230. doi: 10.1021/acs.orglett.1c01032. Epub 2021 Apr 2.
Abstract
The Banert cascade of propargylic azides can be promoted by simple silver salts, and the triazafulvene intermediate can be intercepted by carbon nucleophiles. Various indoles (>25 examples, up to 92% yield) and electron-rich heterocycles were effective. The Mayr nucleophilicity parameter () was found to correlate to the reaction efficiency, which enabled the formation of C-C and C-C bonds under otherwise identical conditions from structurally dissimilar nucleophiles.
摘要
炔丙基叠氮化物的巴纳特级联反应可由简单的银盐促进，三氮杂富烯中间体可被碳亲核试剂捕获。各种吲哚（>25个实例，产率高达92%）和富电子杂环都是有效的。发现迈尔亲核性参数（）与反应效率相关，这使得在其他条件相同的情况下，能够由结构不同的亲核试剂形成碳-碳键和碳-杂键。
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