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Issue 6, 2021
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Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes

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Abstract

The manipulation of amino C–H bonds has garnered significant interest from the synthetic community due to its inherently high atom, step and redox economy. This Tutorial Review summarises the ability of boranes to mediate hydride abstraction from α-amino and γ-amino conjugated C–H bonds. Borane-mediated hydride abstraction results in the generation of reactive iminium hydridoborate salts that participate in a variety of stoichiometric and catalytic processes. The reactions that have utilised this unusual reactivity include those that manipulate amino scaffolds (including dehydrogenation, racemisation, isomerisation, α- and β-functionalisation, and C–N bond cleavage) and those that use amine-based reagents (transfer hydrogenation, and alkylation).

Graphical abstract: Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes

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Article information


Submitted
05 Sep 2020
First published
03 Feb 2021

This article is Open Access

Chem. Soc. Rev., 2021,50, 3720-3737
Article type
Tutorial Review

Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes

S. Basak, L. Winfrey, B. A. Kustiana, R. L. Melen, L. C. Morrill and A. P. Pulis, Chem. Soc. Rev., 2021, 50, 3720
DOI: 10.1039/D0CS00531B

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