Nucleophilic trifluoromethylation and difluorination of substituted aromatic aldehydes with Ruppert's and Deoxofluor™ reagents

被引：26

作者：

Singh, RP ^{[1
]}

Chakraborty, D ^{[1
]}

Shreeve, JM ^{[1
]}

机构：

[1] Univ Idaho, Dept Chem, Moscow, ID 83844 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2001年 / 111卷 / 02期

基金：

美国国家科学基金会;

关键词：

(trifluoromethyl)trimethylsilane; 2,2,2-trifluoro-1-(N,N-dialkylaminophenyl)-ethanols; 2,2,2-trifluoro-1-(hydroxyaryl)ethanols; bis(2-methoxyethyl)aminosulfur trifluoride; aryldifluoromethane derivatives; Deoxofluor (TM);

D O I：

10.1016/S0022-1139(01)00447-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Efficient, high yield syntheses of 2,2,2-trifluoro-1-(N,N-dialkylaminophenyl)-ethanols (3a, b) and 2,2,2-trifluoro-1-(hydroxyaryl)ethanols (6c-g) by reacting Ruppert's reagent, (trifluoromethyl)trimethylsilane (TMSCF3), with appropriate substrates in the presence of a catalytic amount of cesium fluoride are described. A versatile route to the synthesis of substituted aryl difluoromethane derivatives (8h-1, 10m, 12n, o, 14p) and the reactivity of substituted aromatic aldehydes towards bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor (TM)) were also investigated. (C) 2001 Elsevier Science B.V. All rights reserved.

引用

页码：153 / 160

页数：8

共 40 条

[1]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[2]

Banks R.E., 1994, ORGANOFLUORINE CHEM

[3]

CREARY X, 1978, J ORG CHEM, V43, P5027, DOI 10.1021/jo00420a614

[4]

DMOWSKI W, 1979, P 11 INT S FLUOR CHE