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Palladium‐catalyzed carbonylation of quaternary ammonium halides to tertiary amides
Author(s) -
Lei Yizhu,
Zhang Rui,
Wu Linjuan,
Wu Qing,
Mei Hui,
Li Guangxing
Publication year - 2014
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3126
Subject(s) - chemistry , carbonylation , catalysis , palladium , halide , ammonium , organic chemistry , inorganic chemistry , medicinal chemistry , carbon monoxide
Catalytic carbonylation of quaternary ammonium salts under anhydrous conditions was investigated using palladium catalyst. The carbonylation of tetramethylammonium iodide was chosen as a model reaction and studied systematically. Ligand‐free PdCl 2 showed efficient catalytic performance for this transformation. A palladium catalyst loading as low as 0.05 mol% was sufficient for high yield (96.9%) of N , N ‐dimethylacetamide, corresponding to a turnover frequency of 242 h −1 . Under optimum conditions, several other quaternary ammonium halides were also carbonylated to corresponding tertiary amides in moderate to excellent yields. The catalytic activity of commercial palladium on activated carbon (Pd/C) catalyst was also evaluated. The Pd/C catalyst exhibited high activity for this carbonylation reaction and could be recycled six times with a slight decrease in activity. Furthermore, mechanistic considerations concerning Pd‐catalyzed carbonylation of quaternary ammonium halides were also discussed. Copyright © 2014 John Wiley & Sons, Ltd.