Reductive Cross-Coupling of Nonaromatic, Heterocyclic Bromides with Aryl and Heteroaryl Bromides
† Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States
‡ Pfizer Worldwide Research & Development, Eastern Point Road, Groton, Connecticut 06340, United States
J. Org. Chem., 2014, 79 (12), pp 5771–5780
DOI: 10.1021/jo500905m
Publication Date (Web): June 3, 2014
Copyright © 2014 American Chemical Society
*E-mail: gmolandr@sas.upenn.edu.
Abstract
Reductive cross-coupling allows the direct C–C bond formation between two organic halides without the need for preformation of an organometallic reagent. A method has been developed for the reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl or heteroaryl bromides. The developed conditions use an air-stable Ni(II) source in the presence of a diamine ligand and a metal reductant to allow late-stage incorporation of saturated heterocyclic rings onto aryl halides in a functional-group tolerant manner.
Figures of 1H and 13C NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.
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