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Spiroketal-Based Diphosphine Ligands in Pd-Catalyzed Asymmetric Allylic Amination of Morita-Baylis-Hillman Adducts: Exceptionally High Efficiency and New Mechanism
其他题名螺缩酮骨架双膦配体与钯催化的Morita-Baylis-Hillman加合物的不对称烯丙基胺化: 超高效率和新反应机理
Wang XM(王晓明); Guo PH(郭沛骅); Han ZB(韩召斌); Wang XB(王旭斌); Wang Z(王正); Ding KL(丁奎岭)
2014
发表期刊J. Am. Chem. Soc.
卷号136期号:1页码:405-411
摘要Exceptionally high activity (with a TON up to 4750) of the palladium complexes of SKP ligand was discovered in the catalysis of asymmetric allylic amination of MBH adducts with aromatic amines. A comprehensive mechanistic study indicates that the unique structural features of the SKP ligand, with a long P center dot center dot center dot P distance in its solid-state structure, were favorable for allowing two P atoms to play a bifunctional role in the catalysis. Herein, one of the P atom forms a C-P sigma-bond with the terminal carbon atom of allyl moiety as a Lewis base, and an alternative P atom coordinates to Pd atom. The cooperative action of organo- and organometallic catalysis discovered in the present catalytic system is most likely responsible for its high activity, as well as excellent regio- and enantioselectivities. The mechanism disclosed in the present catalytic system is distinct from most of the currently recognized mechanisms for Pd-catalyzed allylic substitutions.
学科领域金属有机化学
DOI10.1021/ja410707q
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收录类别SCI
语种英语
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被引频次:60[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/39007
专题金属有机化学国家重点实验室
通讯作者Ding KL(丁奎岭)
作者单位中科院上海有机化学研究所
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GB/T 7714
Wang XM,Guo PH,Han ZB,et al. Spiroketal-Based Diphosphine Ligands in Pd-Catalyzed Asymmetric Allylic Amination of Morita-Baylis-Hillman Adducts: Exceptionally High Efficiency and New Mechanism[J]. J. Am. Chem. Soc.,2014,136(1):405-411.
APA 王晓明,郭沛骅,韩召斌,王旭斌,王正,&丁奎岭.(2014).Spiroketal-Based Diphosphine Ligands in Pd-Catalyzed Asymmetric Allylic Amination of Morita-Baylis-Hillman Adducts: Exceptionally High Efficiency and New Mechanism.J. Am. Chem. Soc.,136(1),405-411.
MLA 王晓明,et al."Spiroketal-Based Diphosphine Ligands in Pd-Catalyzed Asymmetric Allylic Amination of Morita-Baylis-Hillman Adducts: Exceptionally High Efficiency and New Mechanism".J. Am. Chem. Soc. 136.1(2014):405-411.
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