Issue 5, 2011

Transition metal-catalyzed cross coupling with N-acyliminium ions derived from quinolines and isoquinolines

Abstract

A Ni(0) catalyst facilitates efficient C–C bond formation between a wide range of π-neutral and π-deficient aryl boronic acids and N-acyliminium precursors derived from quinoline and isoquinoline. The reaction proceeds under mild conditions and is tolerant of common organic functional groups. In addition, a simple one-pot protocol amenable to the direct use of substituted quinolines is described. Consistent with preliminary data revealing a mild, organoboronate-mediated racemization of enantioenriched N-acyliminium precursors, initial results indicate that a chiral phosphoramidite-ligated nickel catalyst promotes enantioselective arylation of racemic substrate with no evidence of a kinetic resolution during catalysis.

Graphical abstract: Transition metal-catalyzed cross coupling with N-acyliminium ions derived from quinolines and isoquinolines

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Jan 2011
Accepted
07 Feb 2011
First published
21 Feb 2011

Chem. Sci., 2011,2, 980-984

Transition metal-catalyzed cross coupling with N-acyliminium ions derived from quinolines and isoquinolines

T. J. A. Graham, J. D. Shields and A. G. Doyle, Chem. Sci., 2011, 2, 980 DOI: 10.1039/C1SC00026H

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