Synthesis of Trifluoromethylated Alkenes: Hypervalent Iodine Meets High-Valent Copper.

Autor: Milzarek TM; Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL, SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland., Waser J; Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL, SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Aug 14; Vol. 62 (33), pp. e202306128. Date of Electronic Publication: 2023 Jul 10.
DOI: 10.1002/anie.202306128
Abstrakt: The first trifluoromethylation of vinylbenziodoxolones (VBX) is reported herein. The synthetic method is based on the use of bench-stable, high-valent copper(III) species, and the reaction can be initiated under thermal conditions and/or irradiation (365 nm) giving access to trifluoromethylated alkenes in a stereoselective fashion. Various VBX reagents derived from tyrosine, cysteine, small peptides, thiols and amides can be used as precursors. The obtained alkenes could be further functionalized by reduction or epoxidation of the trifluoromethylated double bond. Furthermore, the method could be applied in a large-scale batch/flow synthesis and could be conducted under visible light irradiation.
(© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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