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  • Highly selective nickel-catalyzed three-component coupling of alkynes with enones and alkenyl boronic acids: a novel route to substituted 1,3-dienes.

Highly selective nickel-catalyzed three-component coupling of alkynes with enones and alkenyl boronic acids: a novel route to substituted 1,3-dienes.

Organic letters (2010-08-14)
Chun-Ming Yang, Masilamani Jeganmohan, Kanniyappan Parthasarathy, Chien-Hong Cheng
RESUMO

A highly regio- and stereoselective nickel-catalyzed three-component coupling of alkynes with enones and alkenyl boronic acids to afford highly substituted 1,3-dienes is described. The reaction can also be extended to cyclization of enynes with coupling to alkenyl boronic acids. A possible reaction mechanism involving a five-membered nickelacycle as a key intermediate is proposed.

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Sigma-Aldrich
trans-1-Propen-1-ylboronic acid, ≥95.0%