Synthesis 2018; 50(16): 3205-3216
DOI: 10.1055/s-0037-1609575
special topic
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Decarboxylative Benzylation of Acetylides and Enolates

Robert R. P. Torregrosa
The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Dr., Lawrence, KS 66045, USA   Email: tunge@ku.edu
,
Shehani N. Mendis
The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Dr., Lawrence, KS 66045, USA   Email: tunge@ku.edu
,
Alex Davies
The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Dr., Lawrence, KS 66045, USA   Email: tunge@ku.edu
,
Jon A. Tunge*
The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Dr., Lawrence, KS 66045, USA   Email: tunge@ku.edu
› Author Affiliations
We thank the National Science Foundation (CHE-1465172) and the Kansas Bioscience Authority Rising Star program for financial support. Support for the NMR instrumentation was provided by NSF Academic Research Infrastructure Grant No. 9512331, NIH Shared Instrumentation Grant No. S10RR024664, and NSF Major Research Instrumentation Grant No. 0320648.
Further Information

Publication History

Received: 15 May 2018

Accepted after revision: 14 June 2018

Publication Date:
30 July 2018 (eFirst)

Published as part of the Special Topic Modern Coupling Approaches and their Strategic Applications in Synthesis

Abstract

Benzylic alkylation of enolates and acetylides has been achieved through the use of a decarboxylative benzylation strategy. Previous research in this area is often limited by the need for extended conjugation in the electrophiles that are coupled. Herein, we report that the use of 1,1'-bis(diphenylphosphino)ferrocene (dppf) ligand allows the coupling of simple benzyl electrophiles with enolates, while the use of XPhos ligand promotes the decarboxylative couplings of propiolates.

Supporting Information

 
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