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Reactions of biologically inspired hydride sources with B(C6F5)3

Wilkins, Lewis C., Santi, Nicolo ORCID:, Luk, Louis Y. P. ORCID: and Melen, Rebecca L. ORCID: 2017. Reactions of biologically inspired hydride sources with B(C6F5)3. Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences 375 (2101) , 20170009. 10.1098/rsta.2017.0009

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The combination of 1-benzyl-1,4-dihydropyridines with the strong Lewis acid, B(C6F5)3, generates a stable pyridinium borohydride species in high yields (94%) in as little as 10 min. This use of biologically inspired hydride sources further builds on the recent work of new hydride donors in the formation of borohydrides. When functionalizing the dihydropyridine with an amide or carboxylic acid moiety, a disproportionation reaction composed of a series of protonation/reduction steps is observed upon the addition of B(C6F5)3. As a result, one equivalent of dihydropyridine undergoes net hydrogenation, whereas the other is dehydrogenated yielding the pyridinium counterpart in a transfer hydrogenation-type mechanism.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: The Royal Society
ISSN: 1364-503X
Funders: Wellcome trust
Date of First Compliant Deposit: 12 September 2017
Date of Acceptance: 24 July 2017
Last Modified: 07 May 2023 01:31

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