New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols

被引：30

作者：

Foth, Paul J. ^{[1
]}

Gu, Frances ^{[1
]}

Bolduc, Trevor G. ^{[1
]}

Kanani, Sahil S. ^{[1
]}

Sammis, Glenn M. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada

来源：

CHEMICAL SCIENCE | 2019年 / 10卷 / 44期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ALPHA-FLUORINATED ETHERS; SN2; REACTIVITY; HALOGEN ATOMS; SUBSTITUTION; NUCLEOPHILES; THIOETHERS; CHEMISTRY; MOLECULE; AMINES; SUFEX;

D O I：

10.1039/c9sc03570b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report a new method for the one-pot synthesis of 1,1-dihydrofluoroalkyl sulfides by bubbling sulfuryl fluoride (SO2F2) through a solution of the corresponding alcohol and thiol. The reaction proceeds through a new class of bis(1,1-dihydrofluoroalkyl) sulfate reagents, to afford the desired 1,1-dihydrofluoroalkyl sulfides in 55-90% isolated yields. The bis(1,1-dihydrofluoroalkyl) sulfates are highly chemoselective for thiol alkylation, and are unreactive with competing, unprotected nucleophiles, including amines, alcohols, and carboxylic acids.

引用

页码：10331 / 10335

页数：5

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