Insertion of Nitriles into Zirconocene 1-aza-1,3-diene Complexes: Chemoselective Synthesis of N-H and N-Substituted Pyrroles

被引：30
作者：
Yu, Shasha [1 ]
Xiong, Meijun [1 ]
Xie, Xin [1 ]
Liu, Yuanhong [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 43期
基金：
中国国家自然科学基金;
关键词：
azazirconacycles; cyclization; insertion; nitriles; pyrroles; MEDIATED MULTICOMPONENT REACTIONS; HIGHLY STEREOSELECTIVE-SYNTHESIS; CARBON BOND-CLEAVAGE; COUPLING REACTIONS; CONJUGATED 1,3-BUTADIYNES; TETHERED DIYNES; C BONDS; TITANIUM; DERIVATIVES; ZIRCONIUM;
D O I：
10.1002/anie.201407221
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The direct insertion of nitriles into zirconocene-1-aza-1,3-diene complexes provides an efficient, chemoselective, and controllable synthesis of N-H and N-substituted pyrroles upon acidic aqueous work-up. The outcome of the reaction (that is, the formation of N-H or N-substituted pyrroles) results from the different cyclization patterns, which depend on the relative stability and reactivity of the enamine-imine tautomers formed by hydrolysis of the diazazirconacycles.
引用
收藏
页码：11596 / 11599
页数：4
相关论文
共 64 条
[1]  
[Anonymous], ANGEW CHEM
[2]   AN EASY ENTRY TO 4-SUBSTITUTED 1-AZA-1,3-DIENES FROM SIMPLE ALLYLIC AMINES [J].
BARLUENGA, J ;
SANZ, R ;
GONZALEZ, R ;
FANANAS, FJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (08) :989-990
[3]  
Bergman J., 2008, COMPREHENSIVE HETERO, V3, P269
[4]   A GENERAL-METHOD FOR THE PREPARATION OF ZIRCONOCENE COMPLEXES OF SUBSTITUTED BENZYNES - INSITU GENERATION, COUPLING REACTIONS, AND USE IN THE SYNTHESIS OF POLYFUNCTIONALIZED AROMATIC-COMPOUNDS [J].
BUCHWALD, SL ;
WATSON, BT ;
LUM, RT ;
NUGENT, WA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7137-7141
[5]   Dialkyltitanium-mediated titanation of conjugated 1,3-butadiynes and its coupling reactions with aldehydes: a facile synthesis of stereodefined enynes and trans-enynols [J].
Chen, Jingjin ;
Liu, Yuanhong .
TETRAHEDRON LETTERS, 2008, 49 (47) :6655-6658
[6]   Carbon-Carbon Bond Formation of α-Alkynylzirconacyclopentenes via Cyclization or a Cu/Pd-Mediated Cyclization/Cross-Coupling Sequence with Aryl Iodides [J].
Chen, Jingjin ;
Li, Yuxue ;
Gao, Hongjun ;
Liu, Yuanhong .
ORGANOMETALLICS, 2008, 27 (21) :5619-5623
[7]   Highly Stereoselective Synthesis of Trisubstituted cis-[3]Cumulenols from Alkynylated Oxatitanacycles in the Presence of Lewis acids [J].
Chen, Jingjin ;
Liu, Yuanhong .
ORGANOMETALLICS, 2010, 29 (02) :505-508
[8]   TITANACYCLES DERIVED FROM REDUCTIVE COUPLING OF NITRILES, ALKYNES, ACETALDEHYDE, AND CARBON-DIOXIDE WITH BIS(PENTAMETHYLCYCLOPENTADIENYL)(ETHYLENE)TITANIUM(II) [J].
COHEN, SA ;
BERCAW, JE .
ORGANOMETALLICS, 1985, 4 (06) :1006-1014
[9]   1-AZADIENE COMPLEXES OF ZIRCONOCENE [J].
DAVIS, JM ;
WHITBY, RJ ;
JAXACHAMIEC, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (24) :1743-1745
[10]  
Enders D, 1998, ANGEW CHEM INT EDIT, V37, P1673, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1673::AID-ANIE1673>3.0.CO
1234567