New hypervalent iodine reagents for electrophilic trifluoromethylation and their precursors: synthesis, structure, and reactivity

被引：74

作者：

Niedermann, Katrin ^{[1
]}

Welch, Jan M. ^{[1
]}

Koller, Raffael ^{[1
]}

Cvengros, Jan ^{[1
]}

Santschi, Nico ^{[1
]}

Battaglia, Philip ^{[1
]}

Togni, Antonio ^{[1
]}

机构：

[1] ETH, Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland

来源：

TETRAHEDRON | 2010年 / 66卷 / 31期

基金：

瑞士国家科学基金会;

关键词：

Trifluoromethylation; Hypervalent iodine; X-ray analysis; Reactivity study; Monochloroiodane; CHEMISTRY; ALCOHOLS;

D O I：

10.1016/j.tet.2010.04.125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several new five- and a six-membered heterocyclic monochloroiodanes, including two cationic species, were synthesized. Three of which were used for the preparation of corresponding trifluoromethylation reagents. These compounds were characterized by X-ray crystallography for a comparative structural study. A reactivity study on the trifluoromethylation of para-toluenesulfonic acid has been conducted in order to compare initial rates. Compounds having a longer I-O bond display a higher reactivity. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5753 / 5761

页数：9

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