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Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water

Lookup NU author(s): Emeritus Professor Bernard Golding

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This is the authors' accepted manuscript of an article that has been published in its final definitive form by American Chemical Society, 2018.

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Abstract

Copyright © 2018 American Chemical Society. Hydrogen sulfide (H2S) was evaluated for its peculiar sulfur radical species generated at different pHs and was used under photolytical conditions in aqueous medium for the reduction of 1,2-diols to alcohols. The conversion steps of 1,2-cyclopentanediol to cyclopentanol via cyclopentanone were analyzed, and it was proven that the reaction proceeds via a dual catalytic/radical chain mechanism. This approach was successfully adapted to the reduction of a variety of carbonyl compounds using H2S at pH 9 in water. This work opens up the field of environmental friendly synthetic processes using the pH-driven modulation of reactivity of this simple reagent in water.

Publication metadata

Author(s): Barata-Vallejo S, Ferreri C, Golding BT, Chatgilialoglu C

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2018

Volume: 20

Issue: 14

Pages: 4290-4294

Print publication date: 20/07/2018

Online publication date: 09/07/2018

Acceptance date: 02/04/2018

Date deposited: 08/10/2018

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

Publisher: American Chemical Society

URL: https://doi.org/10.1021/acs.orglett.8b01713

DOI: 10.1021/acs.orglett.8b01713

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