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Mechanistic Insights into the Decarboxylative Electrophilic Trifluoromethylthiolation of β‐Ketocarboxylic Acids
Author(s) -
Guyon Hélène,
Chachig Hélène,
Tognetti Vincent,
Joubert Laurent,
Cahard Dominique
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800305
Subject(s) - chemistry , decarboxylation , electrophile , acetonitrile , domino , hydroxide , catalysis , combinatorial chemistry , ammonium hydroxide , organic chemistry
A metal‐free protocol for the domino trifluoromethylthiolation/decarboxylation of β‐ketocarboxylic acids is described. The catalytic reactions take place in acetonitrile in the presence of aqueous ammonium hydroxide and N ‐trifluoromethylthiosaccharin. The sequence of events and reaction mechanism were established experimentally and using density functional theory calculations. This synthetic method offers a convenient alternative to known routes for the synthesis of α‐trifluoromethylthio‐substituted ketones.