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.
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页数：7
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