Catalyst- and Metal-Free Photo-Oxidative Coupling of Thiols with BrCCl3

Xiaoman Li; Jiali Fan; Dezhi Cui; Hui Yan; Shiquan Shan; Yongna Lu; Xiamin Cheng; Teck Peng Loh

doi:10.1002/ejoc.202200340

Catalyst- and Metal-Free Photo-Oxidative Coupling of Thiols with BrCCl₃

Xiaoman Li, Jiali Fan, Dezhi Cui, Hui Yan, Shiquan Shan, Yongna Lu^*, Xiamin Cheng^*, Teck Peng Loh

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

This paper reported a catalyst- and metal-free method to construct disulfide bond with BrCCl₃ under light irradiation. This clean and mild reaction promoted the oxidative coupling of thiols with wide substrate scope, and is applicable to benzylic, aryl and aliphatic thiols, especially cysteine derivative. The disulfides were obtained in high yields up to 98 %, avoiding the use of heating, strong oxidant, metal reagent or catalyst. This facile strategy will facilitate the synthesis of disulfide compounds.

Original language	English
Article number	e202200340
Journal	European Journal of Organic Chemistry
Volume	2022
Issue number	23
DOIs	https://doi.org/10.1002/ejoc.202200340
Publication status	Published - Jun 20 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry

Keywords

Bromotrichloromethane
Disulfide
Metal free
Photochemistry
Photooxidation

Access to Document

10.1002/ejoc.202200340

Cite this

@article{41a8cdf50b23491e9780839ee6c1e9b3,

title = "Catalyst- and Metal-Free Photo-Oxidative Coupling of Thiols with BrCCl3",

abstract = "This paper reported a catalyst- and metal-free method to construct disulfide bond with BrCCl3 under light irradiation. This clean and mild reaction promoted the oxidative coupling of thiols with wide substrate scope, and is applicable to benzylic, aryl and aliphatic thiols, especially cysteine derivative. The disulfides were obtained in high yields up to 98 \%, avoiding the use of heating, strong oxidant, metal reagent or catalyst. This facile strategy will facilitate the synthesis of disulfide compounds.",

keywords = "Bromotrichloromethane, Disulfide, Metal free, Photochemistry, Photooxidation",

author = "Xiaoman Li and Jiali Fan and Dezhi Cui and Hui Yan and Shiquan Shan and Yongna Lu and Xiamin Cheng and Loh, \{Teck Peng\}",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = jun,

day = "20",

doi = "10.1002/ejoc.202200340",

language = "English",

volume = "2022",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

number = "23",

}

TY - JOUR

T1 - Catalyst- and Metal-Free Photo-Oxidative Coupling of Thiols with BrCCl3

AU - Li, Xiaoman

AU - Fan, Jiali

AU - Cui, Dezhi

AU - Yan, Hui

AU - Shan, Shiquan

AU - Lu, Yongna

AU - Cheng, Xiamin

AU - Loh, Teck Peng

PY - 2022/6/20

Y1 - 2022/6/20

N2 - This paper reported a catalyst- and metal-free method to construct disulfide bond with BrCCl3 under light irradiation. This clean and mild reaction promoted the oxidative coupling of thiols with wide substrate scope, and is applicable to benzylic, aryl and aliphatic thiols, especially cysteine derivative. The disulfides were obtained in high yields up to 98 %, avoiding the use of heating, strong oxidant, metal reagent or catalyst. This facile strategy will facilitate the synthesis of disulfide compounds.

AB - This paper reported a catalyst- and metal-free method to construct disulfide bond with BrCCl3 under light irradiation. This clean and mild reaction promoted the oxidative coupling of thiols with wide substrate scope, and is applicable to benzylic, aryl and aliphatic thiols, especially cysteine derivative. The disulfides were obtained in high yields up to 98 %, avoiding the use of heating, strong oxidant, metal reagent or catalyst. This facile strategy will facilitate the synthesis of disulfide compounds.

KW - Bromotrichloromethane

KW - Disulfide

KW - Metal free

KW - Photochemistry

KW - Photooxidation

UR - http://www.scopus.com/inward/record.url?scp=85132792927&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85132792927&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202200340

DO - 10.1002/ejoc.202200340

M3 - Article

AN - SCOPUS:85132792927

SN - 1434-193X

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 23

M1 - e202200340

ER -