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Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalyst

Santi, Nicolò, Morrill, Louis Christian, Swiderek, Katarzyna, Moliner, Vicent and Luk, Louis Y. P. 2021. Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalyst. Chemical Communications 57 (15) , pp. 1919-1922. 10.1039/D0CC08142F

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Abstract

Here, the streptavidin-biotin technology was applied to enable organocatalytic transfer hydrogenation. By introducing a biotin-tethered pyrrolidine (1) to the tetrameric streptavidin (T-Sav), the resulting hybrid catalyst was able to mediate hydride transfer from dihydro-benzylnicotinamide (BNAH) to α, β-unsaturated aldehydes. Hydrogenation of cinnamaldehyde and some of its aryl-substituted analogues was found to be nearly quantitative. Kinetic measurements revealed that the T-Sav:1 assembly possesses enzyme-like behavior, whereas isotope effect analysis, performed by QM/MM simulations, illustrated the step of hydride transfer is at least partially rate-limiting. These results have proven the concept that T-Sav can be used to host secondary amine-catalyzed transfer hydrogenations.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: Royal Society of Chemistry
ISSN: 1359-7345
Funders: Leverhulme Trust, The Royal Society, Wellcome Trust
Date of First Compliant Deposit: 15 January 2021
Date of Acceptance: 14 January 2021
Last Modified: 19 Mar 2021 09:50
URI: http://orca.cardiff.ac.uk/id/eprint/137693

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