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
收藏
页码：5313 / 5316
页数：4
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