Engaging Nonaromatic, Heterocyclic Tosylates in Reductive Cross-Coupling 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 Medicinal Chemistry, Eastern Point Road, Groton, Connecticut 06340, United States
J. Org. Chem., 2015, 80 (5), pp 2907–2911
DOI: 10.1021/acs.joc.5b00135
Publication Date (Web): February 25, 2015
Copyright © 2015 American Chemical Society
*E-mail: gmolandr@sas.upenn.edu.
Abstract
A method has been developed for the introduction of nonaromatic heterocyclic structures onto aryl and heteroaryl bromides using alkyl tosylates in a reductive cross-coupling manifold. This protocol offers an improvement over previous methods by utilizing alkyl tosylate coupling partners that are bench-stable, crystalline solids that can be prepared from inexpensive, commercially available alcohols.
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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