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

Basak, Shyam, Winfrey, Laura, Kustiana, Betty A., Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831, Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531 and Pulis, Alexander P. 2021. Electron deficient borane-mediated hydride abstraction in amines: stoichiometric and catalytic processes. Chemical Society Reviews 50 (6) , pp. 3721-3737. 10.1039/D0CS00531B

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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).

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Cardiff Catalysis Institute (CCI) Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	0306-0012
Funders:	EPSRC (Research fellowship No. EP/R026912/1), Leverhulme Trust (Research Project Grant No. RPG-2015-361), and the Royal Society (Grant No. RGS\R1\191082).
Date of First Compliant Deposit:	11 February 2021
Date of Acceptance:	3 February 2021
Last Modified:	04 May 2023 22:02
URI:	https://orca.cardiff.ac.uk/id/eprint/138468

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