Oxidative Coupling of Terminal Alkynes with Aldehydes Leading to Alkynyl Ketones by Using Indium(III) Bromide

Yohei Ogiwara; Masahito Kubota; Kotaro Kurogi; Takeo Konakahara; Norio Sakai

doi:10.1002/chem.201504255

Oxidative Coupling of Terminal Alkynes with Aldehydes Leading to Alkynyl Ketones by Using Indium(III) Bromide

Chemistry. 2015 Dec 14;21(51):18598-600. doi: 10.1002/chem.201504255. Epub 2015 Nov 5.

Authors

Yohei Ogiwara¹, Masahito Kubota¹, Kotaro Kurogi¹, Takeo Konakahara¹, Norio Sakai²

Affiliations

¹ Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510 (Japan).
² Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510 (Japan). sakachem@rs.noda.tus.ac.jp.

PMID: 26507682
DOI: 10.1002/chem.201504255

Abstract

An indium(III)-promoted direct acylation of terminal alkynes using aldehydes leading to ynones was developed. In contrast to the previous addition reactions of alkynes to aldehydes, which provide propargylic alcohols, the oxidative coupling proceeded exclusively to afford alkynyl ketones. The products were likely generated through an Oppenauer oxidation of the indium propargylic alkoxide species by excess amounts of aldehydes.

Keywords: CC coupling reaction; acylation; alkynes; hydrogen transfer; indium.

Publication types

Research Support, Non-U.S. Gov't