Synthesis of Cyclopalladated Phenyl Imidazoline-Carbene Complexes and Catalytic Study in Suzuki Reaction

doi:10.6023/cjoc201405026

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2304-2308.DOI: 10.6023/cjoc201405026 Previous Articles Next Articles

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环钯化苯基咪唑啉-卡宾络合物的合成及催化Suzuki反应研究

赵雪梅, 肖志强, 梁婷, 高翔, 郝新奇, 宋毛平

郑州大学化学与分子工程学院河南省化学生物与有机化学重点实验室郑州 450001

收稿日期:2014-05-17 修回日期:2014-06-16 发布日期:2014-07-02
通讯作者: 郝新奇,xqhao@zzu.edu.cn;宋毛平,mpsong@zzu.edu.cn E-mail:xqhao@zzu.edu.cn;mpsong@zzu.edu.cn
基金资助:
国家自然科学基金(Nos.21102135, 21272217, J1210060)资助项目.

Synthesis of Cyclopalladated Phenyl Imidazoline-Carbene Complexes and Catalytic Study in Suzuki Reaction

Zhao Xuemei, Xiao Zhiqiang, Liang Ting, Gao Xiang, Hao Xinqi, Song Maoping

College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2014-05-17 Revised:2014-06-16 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

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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]. Chin. J. Org. Chem., 2014, 34(11): 2304-2308.

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环钯化苯基咪唑啉-卡宾络合物的合成及催化Suzuki反应研究

Synthesis of Cyclopalladated Phenyl Imidazoline-Carbene Complexes and Catalytic Study in Suzuki Reaction

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