Citation: Shuo Chen, Qingru Wen, Yanqing Zhu, Yanru Ji, Yu Pu, Zhengli Liu, Yun He, Zhang Feng. Boron-promoted reductive deoxygenation coupling reaction of sulfonyl chlorides for the C(sp³)-S bond construction[J]. Chinese Chemical Letters, ;2022, 33(12): 5101-5105. doi: 10.1016/j.cclet.2022.04.022 shu

Boron-promoted reductive deoxygenation coupling reaction of sulfonyl chlorides for the C(sp³)-S bond construction

Shuo Chen ^{a, 1} ,
Qingru Wen ^{a, 1} ,
Yanqing Zhu ^a ,
Yanru Ji ^b ,
Yu Pu ^{b, *,} ,
Zhengli Liu ^a ,
Yun He ^a ,
Zhang Feng ^{a, b, *,}

a.
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China
b.
Medical Imaging Key Laboratory of Sichuan Province, North Sichuan Medical College, Nanchong 637000, China

puyu@nsmc.edu.cn

fengzh@cqu.edu.cn

Received Date: 8 February 2022
Revised Date: 4 April 2022
Accepted Date: 8 April 2022
Available Online: 12 April 2022

Figures(6)

Herein, we report a borane-promoted reductive deoxygenation coupling reaction to synthesize sulfides. This reaction features excellent functional group compatibility, high efficiency, broad substrate scope, and application in late-stage functionalization of biomolecules. Preliminary mechanistic studies suggest diaryl sulfides are the intermediates of this reaction. Moreover, the real active aryl sulfide anions may be generated in situ with the aid of B₂pin₂ and react with alkyl tosylates through a concerted S_N2 pathway.
- C-S bond formation,
- Reductive deoxygenation coupling,
- Borane,
- Organosulfur compounds,
- Green chemistry
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Boron-promoted reductive deoxygenation coupling reaction of sulfonyl chlorides for the C(sp3)-S bond construction

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通讯作者: 陈斌, bchen63@163.com

Boron-promoted reductive deoxygenation coupling reaction of sulfonyl chlorides for the C(sp³)-S bond construction