Direct C(sp3)-H functionalization with thiosulfonates via photoredox catalysis

Linfeng Liu; Yujian Pang; Canliang Ma; Daiqing Zhou; Wenjie Zhang; Jin Huang; Jie Sun; Jiangkai Qiu; Yihuan Liu; Lei Shen; Zhenjiang Li; Kai Guo

doi:10.1016/j.gresc.2024.05.003

Direct C(sp³)-H functionalization with thiosulfonates via photoredox catalysis

Linfeng Liu, Yujian Pang, Canliang Ma, Daiqing Zhou, Wenjie Zhang, Jin Huang, Jie Sun, Jiangkai Qiu, Yihuan Liu, Lei Shen, Zhenjiang Li, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

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

Abstract

While C(sp³)-S bonds exist in many biologically active compounds, the direct catalytic C(sp³)-H thiolation remains elusive. Herein, we report a convenient and green C(sp³)-H thiolation approach mediated by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst. A wide range of C(sp³)-H bond-containing etheric, allylic, alkyl, ketonic, amidic substrates and sulfonyl-based SOMOphiles participated in the reaction, producing thioethers with high efficiency. The present protocol features green characteristics, such as being free of harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.

Original language	English
Journal	Green Synthesis and Catalysis
DOIs	https://doi.org/10.1016/j.gresc.2024.05.003
State	Accepted/In press - 2024

Keywords

C(sp)-H bond
Continuous-flow technology
Organosulfur molecules
Photoredox catalysis

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10.1016/j.gresc.2024.05.003

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@article{a92d3e3181384633b2af025042246e0a,

title = "Direct C(sp3)-H functionalization with thiosulfonates via photoredox catalysis",

abstract = "While C(sp3)-S bonds exist in many biologically active compounds, the direct catalytic C(sp3)-H thiolation remains elusive. Herein, we report a convenient and green C(sp3)-H thiolation approach mediated by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst. A wide range of C(sp3)-H bond-containing etheric, allylic, alkyl, ketonic, amidic substrates and sulfonyl-based SOMOphiles participated in the reaction, producing thioethers with high efficiency. The present protocol features green characteristics, such as being free of harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.",

keywords = "C(sp)-H bond, Continuous-flow technology, Organosulfur molecules, Photoredox catalysis",

author = "Linfeng Liu and Yujian Pang and Canliang Ma and Daiqing Zhou and Wenjie Zhang and Jin Huang and Jie Sun and Jiangkai Qiu and Yihuan Liu and Lei Shen and Zhenjiang Li and Kai Guo",

note = "Publisher Copyright: {\textcopyright} 2024 Fudan University",

year = "2024",

doi = "10.1016/j.gresc.2024.05.003",

language = "英语",

journal = "Green Synthesis and Catalysis",

issn = "2666-5549",

publisher = "KeAi Communications Co.",

}

TY - JOUR

T1 - Direct C(sp3)-H functionalization with thiosulfonates via photoredox catalysis

AU - Liu, Linfeng

AU - Pang, Yujian

AU - Ma, Canliang

AU - Zhou, Daiqing

AU - Zhang, Wenjie

AU - Huang, Jin

AU - Sun, Jie

AU - Qiu, Jiangkai

AU - Liu, Yihuan

AU - Shen, Lei

AU - Li, Zhenjiang

AU - Guo, Kai

PY - 2024

Y1 - 2024

N2 - While C(sp3)-S bonds exist in many biologically active compounds, the direct catalytic C(sp3)-H thiolation remains elusive. Herein, we report a convenient and green C(sp3)-H thiolation approach mediated by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst. A wide range of C(sp3)-H bond-containing etheric, allylic, alkyl, ketonic, amidic substrates and sulfonyl-based SOMOphiles participated in the reaction, producing thioethers with high efficiency. The present protocol features green characteristics, such as being free of harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.

AB - While C(sp3)-S bonds exist in many biologically active compounds, the direct catalytic C(sp3)-H thiolation remains elusive. Herein, we report a convenient and green C(sp3)-H thiolation approach mediated by using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst. A wide range of C(sp3)-H bond-containing etheric, allylic, alkyl, ketonic, amidic substrates and sulfonyl-based SOMOphiles participated in the reaction, producing thioethers with high efficiency. The present protocol features green characteristics, such as being free of harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.

KW - C(sp)-H bond

KW - Continuous-flow technology

KW - Organosulfur molecules

KW - Photoredox catalysis

UR - http://www.scopus.com/inward/record.url?scp=85200334205&partnerID=8YFLogxK

U2 - 10.1016/j.gresc.2024.05.003

DO - 10.1016/j.gresc.2024.05.003

M3 - 文章

AN - SCOPUS:85200334205

SN - 2666-5549

JO - Green Synthesis and Catalysis

JF - Green Synthesis and Catalysis

ER -

Direct C(sp³)-H functionalization with thiosulfonates via photoredox catalysis

Abstract

Keywords

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