Photoredox catalysed reductive cleavage of dibenzothiophene dioxides enabled by a temperature-controlled photoreactor
Photoredox catalysed reductive cleavage of dibenzothiophene dioxides enabled by a temperature-controlled photoreactor
The cleavage of C–S bonds in dibenzothiophene dioxides under reductive photoredox catalysed conditions is reported. The reactions afford sulfinates, which can be used in a variety of subsequent transformations for diversification. When using unsymmetrical dibenzothiophene substrates, reductive cleavage occurs preferentially at one C–S bond. Experimental and computational studies provide insight into this interesting selectivity. The process tolerates the presence of oil (dodecane), highlighting a possible application in the removal of dibenzothiophene impurities from crude oil. The reactivity of some substrates is highly dependent on reaction temperature, hence the development of a versatile and inexpensive 3D printed photoreactor that allows for the precise control of reaction temperature is also reported.
Wang, Siyuan
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Le, Quang Truong
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Shishido, Yoshiteru
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Kokculer, Ismail Y.
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Yamazaki, Ken
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Perry, Gregory J.P.
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Nightingale, Adrian M.
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Yorimitsu, Hideki
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Wang, Siyuan
146e7d4a-2178-405f-bb89-19871eb6d6b1
Le, Quang Truong
f992d90c-d3fb-4d33-b3fa-d5f07ea5a6f6
Shishido, Yoshiteru
f18611e1-eb0a-4bd9-9124-d3c5be898af6
Kokculer, Ismail Y.
b131f57c-ffbe-4184-9c01-77bc95123363
Yamazaki, Ken
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Perry, Gregory J.P.
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Nightingale, Adrian M.
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Yorimitsu, Hideki
5790badd-1359-473d-b584-a4a57406574e
Wang, Siyuan, Le, Quang Truong, Shishido, Yoshiteru, Kokculer, Ismail Y., Yamazaki, Ken, Perry, Gregory J.P., Nightingale, Adrian M. and Yorimitsu, Hideki
(2025)
Photoredox catalysed reductive cleavage of dibenzothiophene dioxides enabled by a temperature-controlled photoreactor.
Chemical Science.
(doi:10.1039/D5SC05889A).
Abstract
The cleavage of C–S bonds in dibenzothiophene dioxides under reductive photoredox catalysed conditions is reported. The reactions afford sulfinates, which can be used in a variety of subsequent transformations for diversification. When using unsymmetrical dibenzothiophene substrates, reductive cleavage occurs preferentially at one C–S bond. Experimental and computational studies provide insight into this interesting selectivity. The process tolerates the presence of oil (dodecane), highlighting a possible application in the removal of dibenzothiophene impurities from crude oil. The reactivity of some substrates is highly dependent on reaction temperature, hence the development of a versatile and inexpensive 3D printed photoreactor that allows for the precise control of reaction temperature is also reported.
Text
ChemSci_SW_251020_Pure
- Accepted Manuscript
Text
d5sc05889a
- Version of Record
More information
Accepted/In Press date: 22 October 2025
e-pub ahead of print date: 23 October 2025
Identifiers
Local EPrints ID: 507275
URI: http://eprints.soton.ac.uk/id/eprint/507275
ISSN: 1478-6524
PURE UUID: 040a3da8-def8-4bfa-afb2-491bcd40cf69
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Date deposited: 02 Dec 2025 18:12
Last modified: 03 Dec 2025 03:05
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Contributors
Author:
Siyuan Wang
Author:
Quang Truong Le
Author:
Yoshiteru Shishido
Author:
Ismail Y. Kokculer
Author:
Ken Yamazaki
Author:
Gregory J.P. Perry
Author:
Adrian M. Nightingale
Author:
Hideki Yorimitsu
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