Abstract
In the molecule of the title N,N′-disubstituted imidazol-2-ylidene palladium(II) complex, [PdBr2(C21H24N4O)]·CH2Cl2, the palladium(II) atom adopts a slightly distorted square-planar coordination (r.m.s. deviation = 0.0145 Å), and the five-membered chelate ring is almost planar [maximum displacement = 0.015 (8) Å]. The molecular conformation is enforced by intramolecular C—H...Br hydrogen bonds. In the crystal, complex molecules and dichloromethane molecules are linked into a three-dimensional network by C—H...O and C—H...Br hydrogen bonds.
Highlights
In the molecule of the title N,N0-disubstituted imidazol-2-ylidene palladium(II) complex, [PdBr2(C21H24N4O)]ÁCH2Cl2, the palladium(II) atom adopts a slightly distorted square-planar coordination (r.m.s. deviation = 0.0145 A ), and the fivemembered chelate ring is almost planar [maximum displacement = 0.015 (8) A ]
The molecular conformation is enforced by intramolecular C—HÁ Á ÁBr hydrogen bonds
Complex molecules and dichloromethane molecules are linked into a three-dimensional network by C—HÁ Á ÁO and C—HÁ Á ÁBr hydrogen bonds
Summary
N-Heterocyclic carbenes (NHCs) have been widely used as ancillary ligands in coordination chemistry and organic catalysis since the successful isolation and characterization of the first stable NHC by Arduengo (Arduengo et al, 1991). Chelating NHC metal complexes containing heteroatom donors, such as P, N, O and S, have been synthesized, characterized and employed extensively as catalysts for organic transformations (Ahrens et al, 2006; Bierenstiel & Cross, 2011; Meyer et al, 2012; Peris & Crabtree, 2004). Our group has developed an efficient procedure for the synthesis of chiral imidazole derivatives carrying hydroxyalkyl or amide functional groups (Mao et al, 2010). Through simple quaternization by 2-bromopyridine or 2-chloropyrimidine, heterodifunctionalized imidazolium salts were obtained. Direct metallation of the heterodifunctionalized imidazolium salts by Pd(OAc) under mild reaction condition produced the CNHC,N-chelating palladium complexes smoothly (Yang et al, 2015; Yang, Zhang, Xiao & Mao, 2016; Yang, Zhang, Yuan et al, 2016).
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