Direct Nucleophilic Trifluoromethylation of Carbonyl Compounds by Potent Greenhouse Gas, Fluoroform: Improving the Reactivity of Anionoid Trifluoromethyl Species in Glymes

Overview

Journal Sci Rep

Specialty Science

Date 2018 Aug 2

PMID 30065282

Citations 11

Authors

Takuya Saito

Jiandong Wang

Etsuko Tokunaga

Seiji Tsuzuki

Norio Shibata

Affiliations

Soon will be listed here.

Abstract

A simple protocol to overcome the problematic trifluoromethylation of carbonyl compounds by the potent greenhouse gas "HFC-23, fluoroform" with a potassium base is described. Simply the use of glymes as a solvent or an additive dramatically improves the yields of this transformation. Experimental results and DFT calculations suggest that the beneficial effect deals with glyme coordination to the K to produce [K(polyether)] whose diminished Lewis acidity renders the reactive anionoid CF counterion species more 'naked', thereby slowing down its undesirable decomposition to CF and F and simultaneously increasing its reactivity towards the organic substrate.

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