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Pd-Catalyzed Boroperfluoroalkylation of Alkynes Opens a Route to One-Pot Reductive Carboperfluoroalkylation of Alkynes with Perfluoroalkyl and Aryl Iodides

Author:
Domański, Sylwester, Gatlik, Beata, Chaładaj, Wojciech
Source:
Organic letters 2019 v.21 no.13 pp. 5021-5025
ISSN:
1523-7052
Subject:
Lewis acids, additives, alkenes, alkynes, catalysts, catalytic activity, chemical reactions, chemical structure, iodides, organoiodine compounds, palladium, perfluorocarbons, stereoselectivity, temperature
Abstract:
A three-component tandem Pd-catalyzed perfluoroalkylative borylation of terminal and internal alkynes is presented. On the basis of this methodology, the first reductive dicarbofunctionalization of alkynes with two electrophiles (perfluoroalkyl and aryl iodides) through a temperature-controlled sequence of iodoperfluoroalkylation–borylation coupling is developed. This regio- and stereoselective process is easily controllable by a temperature program, providing access to fluoroalkyl-substituted vinyl iodides, vinyl boronates, or olefins from the very same complex reaction mixture (four substrates, catalysts, base, and additives).
Agid:
6496888