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American Chemical Society, Journal of Organic Chemistry, 14(80), p. 7226-7234, 2015

DOI: 10.1021/acs.joc.5b01227

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Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles

Journal article published in 2015 by Silvia Gazzola, Egle M. Beccalli, Tea Borelli, Carlo Castellano ORCID, Maria Assunta Chiacchio, Daria Diamante, Gianluigi Broggini
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

A highly effective synthesis of haloalkylidene-substituted heterocycles by copper(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of Nhalosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl2 and CuBr2, respectively.