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Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates

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Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States
Cite this: Org. Lett. 2016, 18, 1, 136–139
Publication Date (Web):December 17, 2015
https://doi.org/10.1021/acs.orglett.5b03455
Copyright © 2015 American Chemical Society

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    Abstract

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    We have developed a stereospecific, nickel-catalyzed cross-coupling of secondary benzylic ammonium salts and diboronate esters to deliver highly enantioenriched benzylic boronates. This reaction utilizes amine-derived electrophiles, which are readily available in high enantiopurity, and simple, inexpensive nickel catalysts. This reaction has broad scope, enabling synthesis of a variety of secondary benzylic boronates in good yields and excellent ee’s.

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