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Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles

Wang, Zhaobin and Bachman, Shoshana and Dudnik, Alexander S. and Fu, Gregory C. (2018) Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles. Angewandte Chemie International Edition, 57 (44). pp. 14529-14532. ISSN 1433-7851. http://resolver.caltech.edu/CaltechAUTHORS:20180806-125754691

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Abstract

Nickel‐catalyzed cross‐coupling has emerged as the most versatile approach to date for achieving enantioconvergent carbon–carbon bond formation using racemic alkyl halides as electrophiles. In contrast, there have not yet been reports of the application of chiral nickel catalysts to the corresponding reactions with heteroatom nucleophiles to produce carbon–heteroatom bonds with good enantioselectivity. Herein, we establish that a chiral nickel/pybox catalyst can borylate racemic secondary benzylic chlorides to provide enantioenriched benzylic boronic esters, a highly useful family of compounds in organic synthesis. The method displays good functional group compatibility (e.g., being unimpeded by the presence of an indole, a ketone, a tertiary amine, or an unactivated alkyl bromide), and both of the catalyst components (NiCl_2⋅glyme and the pybox ligand) are commercially available.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.201806015DOIArticle
ORCID:
AuthorORCID
Fu, Gregory C.0000-0002-0927-680X
Additional Information:© 2018 John Wiley & Sons. Manuscript received: May 24, 2018; Revised manuscript received: July 10, 2018; Accepted manuscript online: August 5, 2018; Version of record online: August 19, 2018. Special Issue: 150th Anniversary of the Technical University of Munich. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, grant R01-GM062871). We thank Dr. Scott C. Virgil, Dr. David G. VanderVelde, Dr. Xin Mu, and Dr. Yufan Liang for assistance and helpful discussions. The authors declare no conflict of interest.
Funders:
Funding AgencyGrant Number
NIHR01-GM062871
Subject Keywords:asymmetric catalysis • boron • cross-coupling • nickel
Record Number:CaltechAUTHORS:20180806-125754691
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20180806-125754691
Official Citation:Z. Wang, S. Bachman, A. S. Dudnik, G. C. Fu, Angew. Chem. Int. Ed. 2018, 57, 14529.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88606
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:06 Aug 2018 21:54
Last Modified:25 Oct 2018 16:39

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