Aromatic and Benzylic C-H Bond Functionalization Upon Reaction between Nitriles and Perfluoroalkyl Sulfoxides

被引：22

作者：

Mace, Yohan ^{[1
]}

Urban, Celine ^{[1
]}

Pradet, Charlotte ^{[2
]}

Blazejewski, Jean-Claude ^{[1
]}

Magnier, Emmanuel ^{[1
]}

机构：

[1] Univ Versailles, Inst Lavoisier Versailles, CNRS, UMR 8180, F-78035 Versailles, France

[2] GlaxoSmithKline, Synth Chem, Stevenage SG1 2NY, Herts, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 31期

关键词：

Rearrangement; C-H activation; Fluorine; Sulfur; Nitriles; Elimination; TRIFLUOROMETHYLATION; DIFLUOROMETHYLATION; GLYCOSYLATIONS; ANHYDRIDE; SULFIDES; SULFONES; REAGENT;

D O I：

10.1002/ejoc.200900873

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We studied the thermal behavior of some intermediates formed by reaction of nitriles with perfluoroalkyl sulfoxides upon trifluoromethanesulfonic anhydride activation. Bistriflate ketal 3, precursor of sulfilimine 1, may undergo a rearrangement to sulfanyl nitrile 5 after triflic acid elimination under thermal conditions. With p-tolyl trifluoromethyl sulfoxide, remote triflic acid elimination from intermediate 4 leads to benzamide 8 formation. These reactions involve, respectively, selective functionalization of the aromatic ortho C-H bond or the benzylic C-H bond para to the sulfoxide group. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：5313 / 5316

页数：4

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