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. 2015 Jan 21;137(2):608-11.
doi: 10.1021/ja511640g. Epub 2015 Jan 6.

Synthesis of highly functionalized tri- and tetrasubstituted alkenes via Pd-catalyzed 1,2-hydrovinylation of terminal 1,3-dienes

Vaneet Saini  1 , Mark O'Dair, Matthew S Sigman
Affiliations

Synthesis of highly functionalized tri- and tetrasubstituted alkenes via Pd-catalyzed 1,2-hydrovinylation of terminal 1,3-dienes

Vaneet Saini et al. J Am Chem Soc. .

Abstract

An efficient method for the construction of Csp(2)-Csp(3) bond in a regio- and stereoselective fashion involving 1,3-terminal dienes, enol triflates/nonaflates, and sodium formate under Pd(0)-catalysis is described. The three component assembly allows trapping of a π-allyl intermediate, after the initial migratory insertion of the diene, by a hydride source that leads to structurally complex and synthetically challenging tri- and tetrasubstituted alkene building blocks.

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Figures

Scheme 1
Scheme 1. Proposed Pd(0)-Catalyzed 1,2-Hydrovinylation of 1,3-Dienes with Enol Triflates/Nonaflates and a Hydride Source
See this image and copyright information in PMC

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