Organic Letters 2010-08-20

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

Chun-Ming Yang, Masilamani Jeganmohan, Kanniyappan Parthasarathy, Chien-Hong Cheng

Index: Org. Lett. 12 , 3610-3613, (2010)

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Abstract

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.