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使用溴化铟(III)实现末端炔烃与醛的氧化偶联反应合成炔基酮

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

作者信息

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

机构信息

Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510 (Japan).

出版信息

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

DOI:10.1002/chem.201504255
PMID:26507682
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.

摘要

开发了一种铟(III)促进的末端炔烃与醛的直接酰化反应,生成炔酮。与之前炔烃与醛的加成反应生成炔丙醇不同,该氧化偶联反应专一性地生成炔基酮。产物可能是通过过量醛对铟炔丙醇盐物种进行欧芬脑尔氧化生成的。

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引用本文的文献

1
Ruthenium-Catalyzed C-C Coupling of Terminal Alkynes with Primary Alcohols or Aldehydes: α,β-Acetylenic Ketones (Ynones) via Oxidative Alkynylation.钌催化的末端炔烃与伯醇或醛的 C-C 偶联:通过氧化炔基化生成α,β-乙炔基酮(Ynones)。
Angew Chem Int Ed Engl. 2023 Jun 5;62(23):e202303345. doi: 10.1002/anie.202303345. Epub 2023 Apr 26.