Intermolecular alkyne hydroaminations involving 1,1-disubstituted hydrazines

被引：164

作者：

Cao, CS ^{[1
]}

Shi, YH ^{[1
]}

Odom, AL ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 17期

关键词：

D O I：

10.1021/ol0201052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Two readily prepared catalysts have been developed for the hydroamination of alkynes by 1,1-disubstituted hydrazines. The catalyses are facile with terminal alkynes and some internal alkynes. If the hydrazine bears an aryl group, Fischer cyclization can occur in a one-pot procedure. In addition, reactions with acetylene to produce a plethora of hydrazones are described. Catalytic reactions involving acetylene and substituted hydrazines are complete in less than 2 h at room temperature and 1 atm of pressure.

引用

页码：2853 / 2856

页数：4

共 58 条

[1] VARIABLE REGIOCHEMISTRY IN THE STOICHIOMETRIC AND CATALYTIC HYDROAMINATION OF ALKYNES BY IMIDOZIRCONIUM COMPLEXES CAUSED BY AN UNUSUAL DEPENDENCE OF THE RATE LAW ON ALKYNE STRUCTURE AND TEMPERATURE [J].

BARANGER, AM ;

WALSH, PJ ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2753-2763

[2] HYDRAZINOMERCURIATION OF TERMINAL ALKYNES AND 3-ALKEN-1-YNES - SYNTHESES OF HYDRAZONES AND 1-AMINO-1-AZA-1,3-DIENES [J].

BARLUENGA, J ;

AZNAR, F ;

LIZ, R ;

BAYOD, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (02) :121-122

[3]

Beller M, 1999, EUR J INORG CHEM, P1121

[4]

Beller M, 1999, CHEM-EUR J, V5, P1306, DOI 10.1002/(SICI)1521-3765(19990401)5:4<1306::AID-CHEM1306>3.3.CO

[5]

2-W

[6] Anti-Markovnikov functionalization of olefins: Rhodium-catalyzed oxidative aminations of styrenes [J].

Beller, M ;

Eichberger, M ;

Trauthwein, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (20) :2225-2227

[7] New cationic rhodium-amine complexes and their implication in the catalytic anti-Markovnikov oxidative amination of styrenes [J].

Beller, M ;

Trauthwein, H ;

Eichberger, M ;

Breindl, C ;

Muller, TE ;

Zapf, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 566 (1-2) :277-285

[8]

Beller M, 2000, CHEM-EUR J, V6, P2513, DOI 10.1002/1521-3765(20000717)6:14<2513::AID-CHEM2513>3.0.CO

[9]

2-V

[10] MONOMERIC METAL-HYDROXIDES, ALKOXIDES, AND AMIDES OF THE LATE TRANSITION-METALS - SYNTHESIS, REACTIONS, AND THERMOCHEMISTRY [J].

BRYNDZA, HE ;

TAM, W .

CHEMICAL REVIEWS, 1988, 88 (07) :1163-1188

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