Formal Asymmetric Hydrobromination of Styrenes Copper-Catalyzed 1,3-Halogen Migration.

Chem Sci

Department of Chemistry, University of Wisconsin, 1101 University Ave. Madison, Wisconsin 53706, United States.

Published: December 2014

An enantioselective Cu(I)-catalyzed 1,3-halogen migration reaction accomplishes a formal hydrobromination by transferring a bromine activating group from a sp carbon to a benzylic carbon in good 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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4494760PMC
http://dx.doi.org/10.1039/C4SC02040EDOI Listing

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