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
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
[11]  
2-A
[12]  
Enders D., 1998, ANGEW CHEM, V110, P1770
[13]   THE REACTION OF (BUTADIENE)ZIRCONOCENE AND (BUTADIENE)HAFNOCENE WITH ETHYLENE [J].
ERKER, G ;
ENGEL, K ;
DORF, U ;
ATWOOD, JL ;
HUNTER, WE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (12) :914-914
[14]   REACTION OF DIENE GROUP-4 METALLOCENE COMPLEXES WITH METAL-CARBONYLS - A NOVEL ENTRY TO FISCHER-TYPE CARBENE COMPLEXES [J].
ERKER, G ;
DORF, U ;
BENN, R ;
REINHARDT, RD ;
PETERSEN, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (24) :7649-7650
[15]   NITRILE ADDITION TO (ETA-4-BUTADIENE)ZIRCONOCENE - THE FORMATION OF ORGANOMETALLIC AND METAL-FREE HEXATRIENEDIAMINE DERIVATIVES [J].
ERKER, G ;
PFAFF, R ;
KRUGER, C ;
NOLTE, M ;
GODDARD, R .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (07) :1669-1673
[16]   FORMATION AND STRUCTURE OF STABLE, ISOLABLE CONJUGATED PRIMARY ENAMINES [J].
ERKER, G ;
PFAFF, R ;
KOWALSKI, D ;
WURTHWEIN, EU ;
KRUGER, C ;
GODDARD, R .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6771-6778
[17]   THE ZIRCONOCENE-INDUCED COUPLING OF BUTADIENE WITH CARBONYL-COMPOUNDS [J].
ERKER, G ;
ENGEL, K ;
ATWOOD, JL ;
HUNTER, WE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (06) :494-495
[18]  
ERKER G, 1983, ANGEW CHEM, V95, P506
[19]  
Erker G., 1982, Angew. Chem, V94, P915
[20]   Anionic multisubstituted 1,2-azaborolyl ligands: Syntheses, characterization, and coordination chemistry [J].
Fang, Xiangdong ;
Assoud, Jalil .
ORGANOMETALLICS, 2008, 27 (11) :2408-2410