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

Beilstein Journal of Organic Chemistry

Pier Alexandre Champagne¹  Jean-François Paquin¹  Mélina Drouin¹  Alexandre Saint-Martin¹ 

[1] Canada Research Chair in Organic and Medicinal Chemistry, CCVC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada G1V 0A6;

关键词: C–F bond activation;    highly concentrated conditions;    nucleophilic substitution;    hydrogen bond;    organofluorine;    triol;   

DOI  :  10.3762/bjoc.9.283

来源: DOAJ

【 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.

【 授权许可】

Unknown