Cyclopentadiene-Phosphine/Palladium-Catalyzed Cleavage of C-N Bonds in Secondary Amines: Synthesis of Pyrrole and Indole Derivatives from Secondary Amines and Alkenyl or Aryl Dibromides

被引：97
作者：
Geng, Weizhi [1 ,2 ]
Zhang, Wen-Xiong [1 ,2 ]
Hao, Wei [1 ,2 ]
Xi, Zhenfeng [1 ,2 ,3 ]
机构：
[1] Peking Univ, Coll Chem, Minist Educ, BNLMS, Beijing 100871, Peoples R China
[2] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[3] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 50期
基金：
中国国家自然科学基金;
关键词：
CARBONYLATIVE RING EXPANSION; PRIMARY ALLYLIC AMINES; CARBON-NITROGEN; OXIDATIVE-ADDITION; REDUCTIVE-ELIMINATION; HETEROCYCLIC CARBENE; ETA(2)(N; C)-PYRIDINE COMPLEX; BENZYLIC SULFONAMIDES; TERMINAL ALKYNES; NICKEL-COMPLEXES;
D O I：
10.1021/ja308950d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient Pd-catalyzed cleavage of C(sp(3))-N bonds in secondary amines and a consequent C(sp(2))-N and C(sp(3))-N coupling process was developed. Various secondary amines could be used to react with alkenyl or aryl dibromides, affording pyrroles and indoles in high yields. Cyclopentadiene-phosphine ligands, a new type of P-olefin ligand, were found to be able to promote the efficiency of this Pd-catalyzed process remarkably. A reactive Pd complex coordinated with a cyclopentadiene-phosphine ligand was successfully isolated and structurally characterized.
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收藏
页码：20230 / 20233
页数：4
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