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Phosphine‐Free, Efficient Double Carbonylation of Aryl Iodides with Amines Catalyzed by Water‐Insoluble and Water‐Soluble N‐Heterocyclic Carbene–Amine Palladium Complexes
Author(s) -
Wang Yan,
Yang Xiaolong,
Zhang Chunyan,
Yu Jianqiang,
Liu Jianhua,
Xia Chungu
Publication year - 2014
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.201400040
Subject(s) - chemistry , phosphine , palladium , carbonylation , carbene , amine gas treating , aryl , catalysis , intramolecular force , organic chemistry , selectivity , medicinal chemistry , ligand (biochemistry) , polymer chemistry , carbon monoxide , biochemistry , alkyl , receptor
The water‐insoluble and water‐soluble N‐heterocyclic carbene (NHC)–amine palladium complexes, Ipr‐Pd(deba)Cl and SO 3 ‐Ipr‐Pd(deba)Cl, were synthesized. Both catalysts exhibit excellent activity in the phosphine‐free double carbonylation of aryl iodides with amines to produce α‐keto amides. Moreover, as the water‐soluble catalyst exhibits significant compatibility in the aqueous phase with the activities of different Pd‐NHC complexes, we conclude that the intramolecular amine ligand strongly affects the selectivity of the products in double carbonylation reaction and serves as an alternative of phosphine ligands.