Chinese Journal of Organic Chemistry >
Synthesis of Cyclopalladated Phenyl Imidazoline-Carbene Complexes and Catalytic Study in Suzuki Reaction
Received date: 2014-05-17
Revised date: 2014-06-16
Online published: 2014-07-02
Supported by
Project supported by the National Natural Science Foundation of China (Nos.21102135, 21272217, J1210060).
The amido alcohols compounds 1a and 1b were synthesized from commercially available 3-nitrobenzoic acid or benzoic acid and (S)-2-amino-3-methyl-1-butanol at room temperature. The amido alcohols, when treated with excess thionyl chloride, followed by p-toluidine, gave the phenyl imidazoline compounds 2a and 2b. Cyclopalladated phenyl imidazoline-carbene complexes 3a and 3b were obtained by the reaction of phenyl imidazolines 2a and 2b with Pd(OAc)2/LiCl followed by treatment with 1,3-dibenzyl-benzimidazolium chloride. All the complexes 3a and 3b were characterized by 1H NMR, 13C NMR, MS and elemental analysis. In the crystal of complex 3a, the compound was assembled to a chain supramolecular structure by the intermolecular hydrogen bonds. And complex 3a presented good catalytic effect on Suzuki reaction.
Key words： cyclopalladated; phenyl imidazoline; carbene complex; crystal structure; Suzuki
Zhao Xuemei , Xiao Zhiqiang , Liang Ting , Gao Xiang , Hao Xinqi , Song Maoping . Synthesis of Cyclopalladated Phenyl Imidazoline-Carbene Complexes and Catalytic Study in Suzuki Reaction[J]. Chinese Journal of Organic Chemistry, 2014 , 34(11) : 2304 -2308 . DOI: 10.6023/cjoc201405026
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