A continuous flow approach to access α-trifluoromethylthiolated esters and amides using commercially available arylacetic acids and N-(trifluoromethylthio)phthalimide as the electrophilic reagent is described. The experimental protocol involves the in-flow conversion of the carboxylic acid into N-acylpyrazole followed by the α-trifluoromethylthiolation in a PTFE coil reactor and final reaction with primary or secondary amines, or alcohols, to afford in a telescoped process α-substituted SCF3 amides and esters, respectively, in good overall yield and short reaction times.

Continuous Flow Synthesis of α-Trifluoromethylthiolated Esters and Amides from Carboxylic Acids: A Telescoped Approach / F. Franco, S. Meninno, A. Lattanzi, A. Puglisi, M. Benaglia. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 86:20(2021 Oct 15), pp. 14207-14212. [10.1021/acs.joc.1c01270]

Continuous Flow Synthesis of α-Trifluoromethylthiolated Esters and Amides from Carboxylic Acids: A Telescoped Approach

A. Puglisi
Penultimo
;
M. Benaglia
Ultimo
2021

Abstract

A continuous flow approach to access α-trifluoromethylthiolated esters and amides using commercially available arylacetic acids and N-(trifluoromethylthio)phthalimide as the electrophilic reagent is described. The experimental protocol involves the in-flow conversion of the carboxylic acid into N-acylpyrazole followed by the α-trifluoromethylthiolation in a PTFE coil reactor and final reaction with primary or secondary amines, or alcohols, to afford in a telescoped process α-substituted SCF3 amides and esters, respectively, in good overall yield and short reaction times.
Alcohols; Esters; Indicators and Reagents; Amides; Carboxylic Acids;
Settore CHIM/06 - Chimica Organica
Enabling TECHNOlogies-driven chemistry: a tailored TRAINing research program for batch and flow synthesis of chiral amino derivatives (TECHNOTRAIN)
PRIN201719LPIGN_01 - Raising up Catalysis for Innovative Developments (SURSUMCAT) - PIGNATARO, LUCA LUIGI - PRIN2017 - PRIN bando 2017 - 2019
27-lug-2021
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/878321
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