Literature DB >> 25828031

Mechanistic studies of copper(I)-catalyzed 1,3-halogen migration.

Ryan Van Hoveln1, Brandi M Hudson2, Henry B Wedler2, Desiree M Bates1, Gabriel Le Gros1, Dean J Tantillo2, Jennifer M Schomaker1.   

Abstract

An ongoing challenge in modern catalysis is to identify and understand new modes of reactivity promoted by earth-abundant and inexpensive first-row transition metals. Herein, we report a mechanistic study of an unusual copper(I)-catalyzed 1,3-migration of 2-bromostyrenes that reincorporates the bromine activating group into the final product with concomitant borylation of the aryl halide bond. A combination of experimental and computational studies indicated this reaction does not involve any oxidation state changes at copper; rather, migration occurs through a series of formal sigmatropic shifts. Insight provided from these studies will be used to expand the utility of aryl copper species in synthesis and develop new ligands for enantioselective copper-catalyzed halogenation.

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Year:  2015        PMID： 25828031      PMCID： PMC4701576          DOI： 10.1021/ja511236d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  56 in total

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