Pincer Thioamide and Pincer Thioimide Palladium Complexes Catalyze Highly Efficient Negishi Coupling of Primary and Secondary Alkyl Zinc Reagents at Room Temperature
文献类型：期刊论文
| 作者 | Wang, Haibo1; Liu, Jing1,2,3,4; Deng, Yi1; Min, Tianyin1; Yu, Ganxiang1; Xu, Xiaojun1; Yang, Zhen2,3,4; Lei, Aiwen1,5 |
| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2009 |
| 卷号 | 15期号:6页码:1499-1507 |
| 关键词 | C-c Coupling Cross-coupling Palladium Tridentate Ligands Zinc |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.200801860 |
| 英文摘要 | Pincer thioamide Pd(II) complex 2 was prepared, and its reaction with cyclohexylzinc chloride yielded novel pincer thioimide Pd(II) complex 3 besides Pd(0) species. The structures of complexes 2 and 3 were confirmed by X-ray analysis. Both complexes are efficient catalysts for Negishi couplings involving primary and secondary alkyl zinc reagents bearing beta-hydrogen atoms. At a concentration of 0.1-0.5 mol% both catalysts readily promoted reactions at room temperature or even at 0 degrees C. The operational simplicity of these processes, in conjunction with the easy accessibility of both catalysts and substrates, promises synthetic utility of this new methodology. An experiment on a scale of 19.35 g carried out at very low catalyst loading of 2 (turnover number: 6.100000) highlighted the potential application of the catalytic system. Monoalkyl and dialkyl zinc reagents displayed different reactivities and selectivities in reactions with aryl iodides catalyzed by complexes 2 or 3, and isomerization in reactions involving acyclic secondary alkyl zinc derivatives was suppressed by using appropriate amounts of dialkyl zinc reagents. Based on preliminary kinetic profiles and reaction evidence, three possible pathways are proposed for the reactions involving acyclic secondary alkyl zinc reagents to rationalize the difference between monoalkyl and dialkyl zinc derivatives. |
| 语种 | 英语 |
| WOS记录号 | WOS:000263093800026 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/65839]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Yang, Zhen |
| 作者单位 | 1.Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China 2.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China 3.Peking Univ, BNLMS, Coll Chem, Beijing 100871, Peoples R China 4.Peking Univ, Lab Chem Genom, State Key Lab Nat & Biominiet Drugs, Shenzhen Grad Sch,Sch Pharmaceut Sci, Beijing 100871, Peoples R China 5.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Haibo,Liu, Jing,Deng, Yi,et al. Pincer Thioamide and Pincer Thioimide Palladium Complexes Catalyze Highly Efficient Negishi Coupling of Primary and Secondary Alkyl Zinc Reagents at Room Temperature[J]. CHEMISTRY-A EUROPEAN JOURNAL,2009,15(6):1499-1507. |
| APA | Wang, Haibo.,Liu, Jing.,Deng, Yi.,Min, Tianyin.,Yu, Ganxiang.,...&Lei, Aiwen.(2009).Pincer Thioamide and Pincer Thioimide Palladium Complexes Catalyze Highly Efficient Negishi Coupling of Primary and Secondary Alkyl Zinc Reagents at Room Temperature.CHEMISTRY-A EUROPEAN JOURNAL,15(6),1499-1507. |
| MLA | Wang, Haibo,et al."Pincer Thioamide and Pincer Thioimide Palladium Complexes Catalyze Highly Efficient Negishi Coupling of Primary and Secondary Alkyl Zinc Reagents at Room Temperature".CHEMISTRY-A EUROPEAN JOURNAL 15.6(2009):1499-1507. |
入库方式： OAI收割
来源：化学研究所
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