Angewandte Chemie (International ed.), 2014-07, Vol.53 (29), p.7629-7633
International ed. in English, 2014
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Details
- Autor(en) / Beteiligte
- Titel
- Copper-Catalyzed One-Pot Trifluoromethylation/Aryl Migration/Carbonyl Formation with Homopropargylic Alcohols
- Ist Teil von
- Angewandte Chemie (International ed.), 2014-07, Vol.53 (29), p.7629-7633
- Auflage
- International ed. in English
- Ort / Verlag
- Weinheim: WILEY-VCH Verlag
- Erscheinungsjahr
- 2014
- Quelle
- MEDLINE
- Beschreibungen/Notizen
- A novel copper‐catalyzed one‐pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargylic alcohols into CF3‐containing 3‐butenal or 3‐buten‐1‐one derivatives in a regioselective manner. Mechanistic studies indicate that the 1,4‐aryl migration proceeds through a radical pathway. A copper‐catalyzed one‐pot reaction of homopropargylic alcohols involves trifluoromethylation, aryl migration, and formation of a carbonyl group. A series of 3‐butenal and 3‐buten‐1‐one derivatives with a trifluoromethyl‐substituted olefin were obtained in moderate to good yields with high regioselectivity. The mechanism is proposed to involve a 5‐ipso cyclization.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 1433-7851eISSN: 1521-3773DOI: 10.1002/anie.201403383Titel-ID: cdi_proquest_miscellaneous_1700976758
- Format
- –
- Schlagworte
- Alcohols, Alcohols - chemistry, Aromatic compounds, aryl migration, Carbonyls, Catalysis, Chlorofluorocarbons, Methane - chemistry, copper, Copper - chemistry, Derivatives, Direct conversion, Formations, Methylation, Migration, Olefins, radical reactions, Radicals, Togni's reagent, trifluoromethylation