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Ligand‐Free Bioinspired Suzuki–Miyaura Coupling Reactions using Aryltrifluoroborates as Effective Partners in Deep Eutectic Solvents
Author(s) -
Dilauro Giuseppe,
García Sergio Mata,
Tagarelli Donato,
Vitale Paola,
Perna Filippo M.,
Capriati Vito
Publication year - 2018
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201801382
Subject(s) - ligand (biochemistry) , eutectic system , chemistry , coupling (piping) , coupling reaction , suzuki reaction , combinatorial chemistry , nanotechnology , palladium , materials science , catalysis , organic chemistry , biochemistry , receptor , alloy , metallurgy
Abstract Pd‐catalyzed Suzuki–Miyaura cross‐coupling between (hetero)aryl halides (Cl, Br, I) and versatile, moisture‐stable mono‐ and bifunctional potassium aryltrifluoroborates proceeded efficiently and chemoselectively in air and under generally mild conditions; a catalyst loading as low as 1 mol % combined with Na 2 CO 3 as a base in choline chloride/glycerol (1:2) deep eutectic solvent (DES) was used as a sustainable and environmentally responsible medium. The catalyst, base, and DES were easily and successfully recycled up to six times with an E‐factor as low as 8.74. Valuable biaryls and terphenyl derivatives were furnished in yields of up to 98 %; over 50 reactions were compared and discussed. The methodology was applied for the synthesis of the nonsteroidal anti‐inflammatory drugs Felbinac and Diflunisal.