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Issue 19, 2020
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Expedient synthesis of conjugated triynes via alkyne metathesis

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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

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Supplementary files

Article information


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

Chem. Sci., 2020,11, 4934-4938
Article type
Edge Article

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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