Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C-S Bond Activation

Xuan Bo Hu; Yuwei Chen; Chen Long Zhu; Hao Xu; Xiaocong Zhou; Weidong Rao; Xiao Chun Hang; Xue Qiang Chu; Zhi Liang Shen

doi:10.1021/acs.joc.4c01786

Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C-S Bond Activation

Xuan Bo Hu, Yuwei Chen, Chen Long Zhu, Hao Xu, Xiaocong Zhou, Weidong Rao, Xiao Chun Hang, Xue Qiang Chu, Zhi Liang Shen

School of Chemistry and Moleculai Engineering

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

8 Scopus citations

Abstract

A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.

Original language	English
Pages (from-to)	13601-13607
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	89
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.4c01786
State	Published - 20 Sep 2024

Access to Document

10.1021/acs.joc.4c01786

Cite this

@article{7fbda0233bb24bf7964908bf9519f8d5,

title = "Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C-S Bond Activation",

abstract = "A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.",

author = "Hu, {Xuan Bo} and Yuwei Chen and Zhu, {Chen Long} and Hao Xu and Xiaocong Zhou and Weidong Rao and Hang, {Xiao Chun} and Chu, {Xue Qiang} and Shen, {Zhi Liang}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = sep,

day = "20",

doi = "10.1021/acs.joc.4c01786",

language = "英语",

volume = "89",

pages = "13601--13607",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C-S Bond Activation

AU - Hu, Xuan Bo

AU - Chen, Yuwei

AU - Zhu, Chen Long

AU - Xu, Hao

AU - Zhou, Xiaocong

AU - Rao, Weidong

AU - Hang, Xiao Chun

AU - Chu, Xue Qiang

AU - Shen, Zhi Liang

PY - 2024/9/20

Y1 - 2024/9/20

N2 - A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.

AB - A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.

UR - http://www.scopus.com/inward/record.url?scp=85203141335&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.4c01786

DO - 10.1021/acs.joc.4c01786

M3 - 文章

AN - SCOPUS:85203141335

SN - 0022-3263

VL - 89

SP - 13601

EP - 13607

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C-S Bond Activation

Abstract

Access to Document

Other files and links

Fingerprint

Cite this