Issue 16, 2017

Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones

Abstract

The reaction of tetraalkynyltin with aldehydes was studied for the first time. The reaction was shown to proceed as a tandem process of nucleophilic addition of tin acetylide to aldehyde followed by Oppenauer-type oxidation of produced tin alcoholates, and may be used as a convenient one-pot approach to acetylenic ketones. The advantages and limitations of the proposed method are discussed.

Graphical abstract: Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones

Supplementary files

Article information

Article type
Paper
Submitted
25 Apr 2017
Accepted
30 Jun 2017
First published
30 Jun 2017
This article is Open Access
Creative Commons BY-NC license

New J. Chem., 2017,41, 8297-8304

Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones

A. S. Levashov, N. A. Aksenov, I. V. Aksenova and V. V. Konshin, New J. Chem., 2017, 41, 8297 DOI: 10.1039/C7NJ01376K

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