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Palladium on Carbon‐Catalyzed Cross‐Coupling using Triarylbismuths
Author(s) -
Monguchi Yasunari,
Hattori Tomohiro,
Miyamoto Yasuhiro,
Yanase Takayoshi,
Sawama Yoshinari,
Sajiki Hironao
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200179
Subject(s) - chemistry , dabco , palladium , aryl , catalysis , coupling reaction , fluoride , medicinal chemistry , halide , octane , ligand (biochemistry) , solvent , caesium , polymer chemistry , inorganic chemistry , organic chemistry , alkyl , biochemistry , receptor
Abstract Simple and efficient protocols for the 10% palladium on carbon (Pd/C)‐catalyzed cross‐coupling reactions between triarylbismuths and aryl halides have been developed. A variety of iodo‐ and bromobenzenes possessing an electron‐withdrawing group on the aromatic nucleus were smoothly cross‐coupled in the presence of 10% Pd/C, sodium phosphate dodecahydrate (Na 3 PO 4 ⋅12 H 2 O) and 1,4‐diazabicyclo[2.2.2]octane (DABCO) in heated N ‐methyl‐2‐pyrrolidone (NMP) as the solvent. For the arylations of iodobenzenes, the reactions effectively proceeded under the combined use of caesium fluoride (CsF) and 2,2′‐biquinoline. Furthermore, a ligand‐free 10% Pd/C‐catalyzed cross‐coupling reaction between the aryl iodides and triarylbismuths was also established by the addition of tetra‐ n ‐buthylammonium fluoride trihydrate (TBAF⋅3 H 2 O) in which the palladium metals were hardly leached from the catalyst into the reaction media.