Synthesis
DOI: 10.1055/s-0037-1610084
special topic
© Georg Thieme Verlag Stuttgart · New York

Vinylation of Benzylic Amines via C–N Bond Functionalization of Benzylic Pyridinium Salts

Weiye Guan
Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA   Email: mpwatson@udel.edu
,
Jennie Liao
Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA   Email: mpwatson@udel.edu
,
Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA   Email: mpwatson@udel.edu
› Author Affiliations
The NIH (R01 GM111820) is gratefully acknowledged. J.L. thanks UD for a University Graduate Fellowship. NMR and other data were acquired at UD on instruments obtained with assistance from NSF and NIH funding (NSF CHE0421224, CHE1229234, CHE0840401, and CHE1048367; NIH P20 GM104316, P20 GM103541, and S10 OD016267).
Further Information

Publication History

Received: 23 March 2018

Accepted after revision: 08 May 2018

Publication Date:
18 June 2018 (eFirst)

W.G. and J.L. are co-first authors.

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

Abstract

Cross-couplings of benzylic pyridinium salts and vinylboronic acids or esters have been developed. Via benzylic pyridinium intermediates, benzylic amines can be engaged in these cross-couplings through C–N bond functionalization. This method boasts mild reaction conditions and excellent tolerance for heteroaryl substituents and a range of functional groups.

Supporting Information

 
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