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Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol

Liu, Zhen and Gao, Yang and Zeng, Tian and Engle, Keary M. (2020) Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol. Israel Journal of Chemistry, 60 (3-4). pp. 219-229. ISSN 0021-2148. https://resolver.caltech.edu/CaltechAUTHORS:20190910-130904956

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Abstract

During the past decade, many research groups have described catalytic methods for 1,2‐carboboration, allowing access to structurally complex organoboronates from alkenes. Various transition metals, especially copper, palladium, and nickel, have been widely used in these reactions. This review summarizes advances in this field, with a special focus on the catalytic cycles involved in different metal‐catalyzed carboboration reactions, as well as the regio‐ and stereochemical consequences of the underlying mechanisms. 1,2‐Carboboration of other unsaturated systems, such as alkynes and allenes, is outside of the scope of this review.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/ijch.201900087DOIArticle
ORCID:
AuthorORCID
Liu, Zhen0000-0002-6313-823X
Gao, Yang0000-0003-2320-2839
Zeng, Tian0000-0001-5957-3442
Engle, Keary M.0000-0003-2767-6556
Additional Information:© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Issue Online: 29 April 2020; Version of Record online: 10 September 2019; Manuscript revised: 20 August 2019; Manuscript received: 09 July 2019. Dedicated to 2019 Wolf Prize Awardees Professor Stephen L. Buchwald and Professor John F. Hartwig. We gratefully acknowledge financial support from the National Institutes of Health (5R35 GM125052‐02). We further thank Bristol‐Myers Squibb (Graduate Fellowship to Z.L.; Unrestricted Grant to K.M.E.) and the Alfred P. Sloan Foundation (Fellowship to K.M.E.). We thank Joseph Derosa and Lucas J. Oxtoby for proofreading the manuscript.
Funders:
Funding AgencyGrant Number
NIH5R35 GM125052-02
Bristol-Myers SquibbUNSPECIFIED
Alfred P. Sloan FoundationUNSPECIFIED
Subject Keywords:1,2-Carboboration; Transition-metal; Alkene; Catalysis; Mechanism
Issue or Number:3-4
Record Number:CaltechAUTHORS:20190910-130904956
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20190910-130904956
Official Citation:Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol. Z. Liu, Y. Gao, T. Zeng, K. M. Engle, Isr. J. Chem. 2020, 60, 219; doi: 10.1002/ijch.201900087
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:98554
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:10 Sep 2019 20:42
Last Modified:29 Oct 2020 21:55

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