Triol-promoted activation of C-F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane

被引：28

作者：

Champagne, Pier Alexandre ^{[1
]}

Saint-Martin, Alexandre ^{[1
]}

Drouin, Melina ^{[1
]}

Paquin, Jean-Francois ^{[1
]}

机构：

[1] Univ Laval, Dept Chem, PROTEO, CCVC, Quebec City, PQ G1V 0A6, Canada

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

C-F bond activation; highly concentrated conditions; nucleophilic substitution; hydrogen bond; organofluorine; triol; PALLADIUM-CATALYZED SUBSTITUTION; ALKYL FLUORIDES; GAS-PHASE; HYDRODEFLUORINATION; REAGENTS; CLEAVAGE;

D O I：

10.3762/bjoc.9.283

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bond-donating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bond-accepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the interaction between the organofluorine compound and the triol. Various benzylic fluorides react with secondary amines or anilines to form benzylic amines in good yields.

引用

页码：2451 / 2456

页数：6

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