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PARK, Jiyong
분자활성 촉매반응 연구단
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Visible-Light-Induced Organophotocatalytic Difunctionallization: Open-Air Hydroxysulfurization of Aryl Alkenes with Aryl Thiols

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Title
Visible-Light-Induced Organophotocatalytic Difunctionallization: Open-Air Hydroxysulfurization of Aryl Alkenes with Aryl Thiols
Author(s)
Hong, Jee Eun; Jung, Yeonghun; Min, Dahye; Jang, Minji; Kim, Soomin; Jiyong Park; Park, Yohan
Publication Date
2022-06
Journal
Journal of Organic Chemistry, v.87, no.11, pp.7378 - 7391
Publisher
American Chemical Society
Abstract
© 2022 American Chemical Society. All rights reserved.Herein, we report a regioselective visible-light-induced organophotoredox catalytic difunctionalization method to prepare β-hydroxysulfides using aryl alkenes and aryl thiols as substrates. The reaction provides a wide substrate scope of aryl alkenes (from simple styrene to complex bioactive compounds) and aryl thiols (from diverse heteroaromatic thiols to nonheteroaromatic thiols) (total 45 examples, up to 88% yield). Based on the combined experimental and computational studies, we demonstrate that in situ generated hydroperoxyl radicals from O2 in air react with benzylic radicals, which restrains the reaction between benzylic radicals and the acidic form of thiols in a classical thiol-ene radical reaction. We show that difunctionalization is possible due to the choice of bases, diluted substrate concentrations, increment in catalyst loading, and selection of suitable aryl thiols under aerobic conditions. Considering the biological importance of heteroaromatic thiols and the lack of methods to install them, our approach offers a platform to derive various β-hydroxysulfides that contain aromatic elements.
URI
https://pr.ibs.re.kr/handle/8788114/12139
DOI
10.1021/acs.joc.2c00595
ISSN
0022-3263
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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