Aminofluorosulfonylation of β,γ-Unsaturated Hydrazones with Sulfur Dioxide and N-Fluorobenzenesulfonimide: Accessing Pyrazoline-Functionalized Aliphatic Sulfonyl Fluorides

被引：12

作者：

Yan, Zhi-Min ^{[1
]}

Qi, Lin ^{[1
]}

Cao, Tong-Yang ^{[1
]}

Liu, Jia-Li ^{[1
]}

Du, Hui-Jie ^{[1
]}

Dong, Yi-Chen ^{[1
]}

Li, Wei ^{[1
]}

Wang, Li-Jing ^{[1
]}

机构：

[1] Hebei Univ, Coll Chem & Mat Sci, Key Lab Med Chem & Mol Diag, Key Lab Chem Biol Hebei Prov,Minist Educ, 180 Wusi Donglu, Baoding 071002, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 21期

基金：

中国国家自然科学基金;

关键词：

SUFEX CLICK CHEMISTRY; CYCLIZATION; ALKENES;

D O I：

10.1021/acs.orglett.3c01278

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient aminofluorosulfonylation strategy was developedforthe synthesis of various pyrazoline-functionalized aliphatic sulfonylfluorides using beta,gamma-unsaturated hydrazoneswith sulfur dioxide and NFSI as the starting materials under mildconditions. The sulfonyl fluoride products could be successfully transformedinto the corresponding sulfonate esters and amides via the sulfur-(VI)fluoride exchange (SuFEx) click reactions. Preliminary mechanisticinvestigations demonstrate that the reaction operates through a radicalcyclization/SO2 insertion/fluorination cascade process.

引用

页码：3910 / 3915

页数：6