Issue 7, 2016

Nickel-catalyzed enantioselective arylation of pyridine

Abstract

We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridinium ions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.

Graphical abstract: Nickel-catalyzed enantioselective arylation of pyridine

Supplementary files

Article information

Article type
Edge Article
Submitted
16 Feb 2016
Accepted
04 Mar 2016
First published
08 Mar 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 4105-4109

Nickel-catalyzed enantioselective arylation of pyridine

J. P. Lutz, S. T. Chau and A. G. Doyle, Chem. Sci., 2016, 7, 4105 DOI: 10.1039/C6SC00702C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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