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

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posted on 2021-02-26, 09:17 authored by Shyam Basak, Laura Winfrey, Betty A Kustiana, Rebecca L Melen, Louis C Morrill, Alexander P Pulis
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).

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Author affiliation

School of Chemistry

Version

  • VoR (Version of Record)

Published in

Chemical Society Reviews

Publisher

The Royal Society of Chemistry

eissn

1460-4744

Copyright date

2021

Available date

2021-02-03

Spatial coverage

England

Language

eng

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