FLUOROAMINE HAVING PERFLUOROALKYL GROUP, PROCESS FOR PRODUCING THE SAME, METHOD OF FLUORINATION THEREWITH, AND METHOD OF RECOVERING AMIDE HAVING PERFLUOROALKYL GROUP
申请人:National University Corporation
Hokkaido University
公开号:EP2022776A1
公开(公告)日:2009-02-11
Provided are a fluorous-tag-introduced fluoroamine of a general formula (I), its production method, a method of fluorination of a substrate having functional group containing oxygen with the fluoroamine serving as a fluorinating agent, and a method of recovering a fluorous-tag-introduced amide after the fluorination. The fluoroamine and its production method, as well as the fluorination method with the fluoroamine and the method of recovery of a fluorous-tag-introduced amide are ecological and advantageous in industrial use, as the load for separating and collecting the product after the fluorination with the fluoroamine serving as a fluorinating agent is small.
(In the formula, R0 is an alkyl group or an aryl group having substituent(s) of Rf-(CH2)m-; Rf is a perfluoroalkyl group; m is from 0 to 2; R1 and R2 each are an alkyl group or an aryl group.)
We prepared a novel fluorous deoxy-fluorination reagent NN-diethyl-alpha,alpha-difluoro-[3,5-bis(1H,1H.2H,2H-perfluorodecyl)benzyl]amine (1b) from 3,5-diiodobenzoic acid (3b) via N,N-diethyl-3,5-bis(1H,1H,2H,2H]perfluorodecyl)benzamide (2b) in four steps and used it for the fluorination of alcohols and diols. After the fluorination reactions, the isolation of the products and recovery of 2b was performed by extraction with a fluorous/organic solvent system. (C) 2008 Elsevier B.V. All rights reserved.