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

Shiquan Shan; Songhao Pang; Yunwei Qu; Yongna Lu; Xiamin Cheng; Lin Li

doi:10.1055/s-0042-1752654

Synlett, Table of Contents

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

^aInstitute 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

^aInstitute 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

^bThe Institute of Flexible Electronics (IFE, Future Technologies), Xiamen University, Xiamen 361005, P. R. of China

,

Yongna Lu

^aInstitute 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∗

^aInstitute 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 ∗

^bThe Institute of Flexible Electronics (IFE, Future Technologies), Xiamen University, Xiamen 361005, P. R. of China

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Abstract

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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.

Key words

photocatalysis - coupling - free radicals - photooxidation - thiols - disulfides

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References

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