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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.

SUBMITTER: Curbet I

PROVIDER: S-EPMC8159245 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Expedient synthesis of conjugated triynes <i>via</i> alkyne metathesis.

Curbet Idriss I Colombel-Rouen Sophie S Manguin Romane R Clermont Anthony A Quelhas Alexandre A Müller Daniel S DS Roisnel Thierry T Baslé Olivier O Trolez Yann Y Mauduit Marc M

Chemical science 20200427 19

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 straightf ...[more]

PMID: 34122949

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