Facile and convenient synthesis of functionalized propargylic alcohols and amines: an InBr₃-Et₃N reagent system promotes the alkynylation of aldehydes and N,O- or N,S-acetals

Norio Sakai*, Reiko Kanada, Maki Hirasawa and Takeo Konakahara

*Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, Noda, Chiba 278-8510, Japan, Email: sakachemrs.noda.tus.ac.jp

N. Sakai, R. Kanada, M. Hirasawa, T. Konakahara, Tetrahedron, 2005, 61, 9298-9304.

DOI: 10.1016/j.tet.2005.07.059

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Abstract

A novel InBr₃-Et₃N reagent system promotes the alkynylation of not only a variety of aromatic/heterocyclic or bulky aliphatic aldehydes but also N,O- or N,S-acetals. The reaction of N-silyl-N,O-acetals with 1-alkynes gives primary propargylic amines in good yields.

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Key Words

Alkynylation, Propargylic alcohols, Propargylic amines, Indium bromide, Acetals

ID: J72-Y2005-3070

Facile and convenient synthesis of functionalized propargylic alcohols and amines: an InBr3-Et3N reagent system promotes the alkynylation of aldehydes and N,O- or N,S-acetals

Norio Sakai*, Reiko Kanada, Maki Hirasawa and Takeo Konakahara

Facile and convenient synthesis of functionalized propargylic alcohols and amines: an InBr₃-Et₃N reagent system promotes the alkynylation of aldehydes and N,O- or N,S-acetals