Pd(OAc)(2)-catalyzed cross-coupling of polyfluoroarenes with simple aromatics in imidazolium ionic liquids (ILs) without oxidant and additive and with recycling/reuse of the IL

Polyfluoroarenes can be cross-coupled with simple aromatics (benzene, toluene, and anisole), in good isolated yields, by using Pd(OAc)(2) dissolved in imidazolium Its [(bmim)PF6 and (bmim)BF4] as solvent, without the need for an oxidant and an additive. The reaction is catalyzed by HOAc and it is su...

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Bibliographic Details
Published inTetrahedron letters Vol. 52; no. 42; pp. 5525 - 5529
Main Authors Kalkhambkar, Rajesh G., Laali, Kenneth K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 19.10.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIRECT ARYLATION
ACID
Polyfluorinated biaryl synthesis
ELECTRON-DEFICIENT POLYFLUOROARENES
ARENES
BROMIDES
Cross-coupling
SOLVENTS
Pd(OAc) in imidazolium IL
ORGANIC-COMPOUNDS
POTASSIUM POLYFLUOROBENZOATES
Polyfluoroarenes
Primary isotope effect
Competitive cross-coupling
LIFE
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Summary:Polyfluoroarenes can be cross-coupled with simple aromatics (benzene, toluene, and anisole), in good isolated yields, by using Pd(OAc)(2) dissolved in imidazolium Its [(bmim)PF6 and (bmim)BF4] as solvent, without the need for an oxidant and an additive. The reaction is catalyzed by HOAc and it is subject to a primary isotope effect (K-H/K-D = 4.87). Competitive cross-coupling reactions of 1,2,4,5-tetrafluorobenzene with benzene/toluene, benzene/anisole, and anisole/toluene gave K-B/K-T = 5.1, K-B/K-A = 5.7, and K-A/K-T = 5.0, respectively, indicative of a remote substituent effect on Pd insertion into the phenyl C-H bond. Mild reaction conditions, simple product isolation and recycling/reuse of the IL are additional advantages of this method. (C) 2011 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2011.08.077