Continuous Flow Synthesis of α-Trifluoromethylthiolated Esters and Amides from Carboxylic Acids: a Telescoped Approach
| Autor: | Sara Meninno, Alessandra Puglisi, Alessandra Lattanzi, Maurizio Benaglia, Francesca Franco |
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| Rok vydání: | 2021 |
| Předmět: |
flow chemistry
Carboxylic acid Carboxylic Acids trifluoromethylthiolation 010402 general chemistry 01 natural sciences Phthalimide chemistry.chemical_compound acyl pyrazoles Organic chemistry chemistry.chemical_classification Primary (chemistry) 010405 organic chemistry Continuous flow Organic Chemistry Esters Flow chemistry Note Amides 0104 chemical sciences flow chemistry trifluoromethylthiolation acyl pyrazoles chemistry Alcohols Reagent Yield (chemistry) Electrophile Indicators and Reagents |
| Zdroj: | The Journal of Organic Chemistry |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.1c01270 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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