Synlett 2024; 35(01): 113-117
DOI: 10.1055/s-0042-1752654
cluster
Functional Dyes

Photooxidative Coupling of Thiols Promoted by Bromo(trichloro)methane in a Basic Aqueous Medium

Shiquan Shan
a   Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering (SCME), Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University (Nanjing Tech), Nanjing 211816, P. R. of China
,
Songhao Pang
a   Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering (SCME), Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University (Nanjing Tech), Nanjing 211816, P. R. of China
,
Yunwei Qu
b   The Institute of Flexible Electronics (IFE, Future Technologies), Xiamen University, Xiamen 361005, P. R. of China
,
Yongna Lu
a   Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering (SCME), Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University (Nanjing Tech), Nanjing 211816, P. R. of China
,
Xiamin Cheng
a   Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering (SCME), Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University (Nanjing Tech), Nanjing 211816, P. R. of China
,
Lin Li
b   The Institute of Flexible Electronics (IFE, Future Technologies), Xiamen University, Xiamen 361005, P. R. of China
› Author Affiliations
This work was supported by Nanjing Tech University (Start-up Grants Nos. 38274017101 and 3827401742).


Abstract

A transition-metal- and organic-solvent-free oxidative coupling of thiols catalyzed by BrCCl3 and NaOH in an aqueous medium with oxygen as a green oxidant was established The facile and green method has a broad substrate scope in converting thiols into the corresponding disulfides with medium to excellent yields (up to 91%). This method could potentially be used to construct bioactive molecules containing disulfide bonds and to label bioactive molecules with disulfide bonds.

Supporting Information



Publication History

Received: 14 January 2023

Accepted: 17 February 2023

Article published online:
31 March 2023

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