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Issue 12, 2014
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Formal asymmetric hydrobromination of styrenes via copper-catalyzed 1,3-halogen migration

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Abstract

An enantioselective Cu(I)-catalyzed 1,3-halogen migration reaction accomplishes a formal hydrobromination by transferring a bromine activating group from a sp2 carbon to a benzylic carbon in good er and with concomitant borylation of the Ar–Br bond. Computational modelling aids in understanding the reaction outcome and suggests future directions to improve the formal asymmetric hydrobromination. The benzyl bromide can be displaced with a variety of nucleophiles to produce a wide array of functionalized products.

Graphical abstract: Formal asymmetric hydrobromination of styrenes via copper-catalyzed 1,3-halogen migration

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Publication details

The article was received on 10 Jul 2014, accepted on 04 Aug 2014 and first published on 04 Aug 2014


Article type: Edge Article
DOI: 10.1039/C4SC02040E
Author version available: Download Author version (PDF)
Citation: Chem. Sci., 2014,5, 4763-4767
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    Formal asymmetric hydrobromination of styrenes via copper-catalyzed 1,3-halogen migration

    R. J. Van Hoveln, S. C. Schmid, M. Tretbar, C. T. Buttke and J. M. Schomaker, Chem. Sci., 2014, 5, 4763
    DOI: 10.1039/C4SC02040E

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