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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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Article information


Submitted
10 Jul 2014
Accepted
04 Aug 2014
First published
04 Aug 2014

Chem. Sci., 2014,5, 4763-4767
Article type
Edge Article
Author version available

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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