Synlett 2016; 27(03): 331-336
DOI: 10.1055/s-0035-1561282
synpacts
© Georg Thieme Verlag Stuttgart · New York

Dehydrogenation Adjacent to Carbonyls Using Palladium–Allyl Intermediates

Aneta Turlik
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, USA   Email: timothy.newhouse@yale.edu
,
Yifeng Chen
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, USA   Email: timothy.newhouse@yale.edu
,
Timothy R. Newhouse*
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, USA   Email: timothy.newhouse@yale.edu
› Author Affiliations
Further Information

Publication History

Received: 27 October 2015

Accepted after revision: 16 November 2015

Publication Date:
23 December 2015 (online)

Abstract

Palladium–allyl chemistry has historically been used as a means of allylation of nucleophiles, as developed by Tsuji and Trost in the 1970s. Also during this decade, the Saegusa oxidation, the most prominent palladium-catalyzed dehydrogenation reaction, was developed. This Synpacts article provides a historical overview of dehydrogenation adjacent to carbonyls and our recent contribution to this area: palladium–allyl catalyzed dehydrogenation of nitriles and esters.

 
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