Issue 19, 2020

Expedient synthesis of conjugated triynes via alkyne metathesis

Abstract

The first synthesis of conjugated triynes by molybdenum-catalysed alkyne metathesis is reported. Strategic to the success of this approach is the utilization of sterically-hindered diynes that allowed for the site-selective alkyne metathesis to produce the desired conjugated triyne products. The steric hindrance of the alkyne moiety was found to be crucial in preventing the formation of diyne byproducts. This novel synthetic strategy was amenable to self- and cross-metathesis providing straightforward access to the corresponding symmetrical and dissymmetrical triynes with high selectivity.

Graphical abstract: Expedient synthesis of conjugated triynes via alkyne metathesis

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Feb 2020
Accepted
24 Apr 2020
First published
27 Apr 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 4934-4938

Expedient synthesis of conjugated triynes via alkyne metathesis

I. Curbet, S. Colombel-Rouen, R. Manguin, A. Clermont, A. Quelhas, D. S. Müller, T. Roisnel, O. Baslé, Y. Trolez and M. Mauduit, Chem. Sci., 2020, 11, 4934 DOI: 10.1039/D0SC01124J

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