Thioethers as Dichotomous Electrophiles for Site-Selective Silylation via C-S Bond Cleavage

被引：13

作者：

Chen, Shuai ^{[1
]}

Guo, Xueying ^{[2
]}

Hou, Haoran ^{[1
]}

Geng, Shasha ^{[1
]}

Liu, Zhengli ^{[1
,3
,4
]}

He, Yun ^{[1
]}

Xue, Xiao-Song ^{[2
]}

Feng, Zhang ^{[1
,3
,4
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China

[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[3] North Sichuan Med Coll, Affiliated Hosp, Nanchong 637503, Peoples R China

[4] Med Imaging Key Lab Sichuan Prov, Nanchong 637503, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 25期

基金：

中国国家自然科学基金;

关键词：

C-S Bond Cleavage; High Selectivity; Iron Catalysis; Silylation; Transition Metal Free; CATALYZED SILYLATION; BORYLATION; NICKEL; ACTIVATION; HYDROSILYLATION; SECONDARY; MILD;

D O I：

10.1002/anie.202303470

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of aryl alkyl sulfides as dichotomous electrophiles for site-selective silylation via C-S bond cleavage has been achieved. Iron-catalyzed selective cleavage of C(aryl)-S bonds can occur in the presence of beta-diketimine ligands, and the cleavage of C(alkyl)-S bonds can be achieved by t-BuONa without the use of transition metals, resulting in the corresponding silylated products in moderate to excellent yields. Mechanistic studies suggest that Fe-Si species may undergo metathesis reactions during the cleavage of C(aryl)-S bonds, while silyl radicals are involved during the cleavage of C(alkyl)-S bonds.

引用

页数：7

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