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1-炔烃、醛和吗啉一锅法合成 1,3-二取代烯丙基。

One-pot synthesis of 1,3-disubstituted allenes from 1-alkynes, aldehydes, and morpholine.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, PR China.

出版信息

J Am Chem Soc. 2010 Feb 17;132(6):1786-7. doi: 10.1021/ja910503k.

Abstract

ZnI(2) has been identified as the catalyst for the one-step synthesis of allenes from terminal alkynes and aldehydes with morpholine as the base in toluene. The reaction is believed to proceed via the intermediacy of propargylic amines, which was converted to allenes by a sequential hydride transfer and beta-elimination process. The reaction is applicable for both aromatic and aliphatic aldehydes. Functionalities such as halide, hydroxyl, or amine may be tolerated.

摘要

ZnI2 被确定为在甲苯中用吗啉作为碱,由末端炔烃和醛一步合成烯丙基化合物的催化剂。该反应被认为是通过丙炔胺中间体进行的,该中间体通过顺序氢转移和β-消除过程转化为烯丙基化合物。该反应适用于芳香族和脂肪族醛。卤素、羟基或胺等官能团可以被容忍。

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