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Synthesis 2018; 50(16): 3231-3237
DOI: 10.1055/s-0037-1610084
DOI: 10.1055/s-0037-1610084
special topic
Vinylation of Benzylic Amines via C–N Bond Functionalization of Benzylic Pyridinium Salts
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 (online)
‡ 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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610084.
- Supporting Information
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See also:
For other transition-metal-catalyzed strategies to 1,3-diaryl allylic products, see:
For reductive, cross-electrophile couplings of benzylic and vinyl electrophiles, see:
For transition-metal-free vinylations, see: