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Triazole‐Functionalized N‐Heterocyclic Carbene Complexes of Palladium and Platinum and Efficient Aqueous Suzuki–Miyaura Coupling Reaction
Author(s) -
Gu Shaojin,
Xu Hui,
Zhang Na,
Chen Wanzhi
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000071
Subject(s) - palladium , carbene , chemistry , medicinal chemistry , aryl , platinum , ligand (biochemistry) , pincer movement , coupling reaction , catalysis , polymer chemistry , organic chemistry , alkyl , biochemistry , receptor
Imidazolium salts bearing triazole groups are synthesized via a copper catalyzed click reaction, and the silver, palladium, and platinum complexes of their N‐heterocyclic carbenes are studied. [Ag 4 (L1) 4 ](PF 6 ) 4 , [Pd(L1)Cl](PF 6 ), [Pt(L1)Cl](PF 6 ) (L1=3‐((1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)methyl)‐1‐(pyrimidin‐2‐yl)‐1H‐imidazolylidene), [Pd 2 (L2) 2 Cl 2 ](PF 6 ) 2 , and [Pd(L2) 2 ](PF 6 ) 2 (L2=1‐butyl‐3‐((1‐(pyridin‐2‐yl)‐1H‐1,2,3‐triazol‐4‐yl)methyl)imidazolylidene) have been synthesized and fully characterized by NMR, elemental analysis, and X‐ray crystallography. The silver complex [Ag 4 (L1) 4 ](PF 6 ) 4 consists of a Ag 4 zigzag chain. The complexes [Pd(L1)Cl](PF 6 ) and [Pt(L1)Cl](PF 6 ), containing a nonsymmetrical NCN ′ pincer ligand, are square planar with a chloride trans to the carbene donor. [Pd 2 (L2) 2 Cl 2 ](PF 6 ) 2 consists of two palladium centers with CN 2 Cl coordination mode, whereas the palladium in [Pd(L2) 2 ](PF 6 ) 2 is surrounded by two carbene and two triazole groups with two uncoordinated pyridines. The palladium compounds are highly active for Suzuki–Miyaura cross coupling reactions of aryl bromides and 1,1‐dibromo‐1‐alkenes in neat water under an air atmosphere.