Ni-Catalyzed Sonogashira Coupling of Nonactivated Alkyl Halides: Orthogonal Functionalization of Alkyl Iodides, Bromides, and Chlorides

摘要

Substituted alkynes are recurring units in numerous natural products, bioactive molecules, and organic materials. They are also versatile synthetic intermediates. During the last decades, Sonogashira coupling has become one of the most widely used methods for the incorporation of alkynyl functionality into organic compounds. It enables the efficient coupling of an organic halide or pseudohalide with a terminal alkyne, normally using a Pd catalyst and a Cu cocatalyst. The electrophilic coupling partners for Sonogashira reactions, however, are generally limited to aryl and vinyl halides and triflates.