Mechanistic Insights into the Decarboxylative Electrophilic Trifluoromethylthiolation of β‐Ketocarboxylic Acids | Zendy

Guyon Hélène | Zendy; Chachig Hélène | Zendy; Tognetti Vincent | Zendy; Joubert Laurent | Zendy; Cahard Dominique | Zendy

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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.

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