Intermolecular cope-type hydroamination of alkenes and alkynes

被引：81

作者：

Beauchemin, Andre M. ^{[1
]}

Moran, Joseph ^{[1
]}

Lebrun, Marie-Eve ^{[1
]}

Seguin, Catherine ^{[1
]}

Dimitrijevic, Elena ^{[1
]}

Zhang, Lili ^{[1
]}

Gorelsky, Serge I. ^{[1
]}

机构：

[1] Univ Ottawa, Ctr Catalysis Res & Innovat, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 08期

关键词：

alkenes; alkynes; green chemistry; hydroamination; solvent effects;

D O I：

10.1002/anie.200703495

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Keep it simple! Intermolecular hydroamination can be achieved simply upon heating alkynes and alkenes with aqueous hydroxylamine. Alkynes react to afford oximes in good to excellent yields, and the formation of Markovnikov products is favored. A mechanism involving Cope-type hydroamination followed by bimolecular proton transfer is suggested and supported by DFT studies. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1410 / 1413

页数：4

共 55 条

[1] Cope elimination: Elucidation of solvent effects from QM/MM simulations [J].

Acevedo, Orlando ;

Jorgensen, William L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) :6141-6146

[2] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[3] Proton-catalyzed hydroamination and hydroarylation reactions of anilines and alkenes: A dramatic effect of counteranions on reaction efficiency [J].

Anderson, LL ;

Arnold, J ;

Bergman, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (42) :14542-14543

[4] Efficient gold-catalyzed hydroamination of 1,3-dienes [J].

Brouwer, C ;

He, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) :1744-1747

[5]

Brouwer C., 2006, ANGEW CHEM, V118, P1776

[6]

Brunet J.J., 2001, CATALYTIC HETEROFUNC, P91

[7] Preparation and X-ray structures of alkyl-titanium(IV) complexes stabilized by indenyl ligands with a pendant ether or amine substituent and their use in the catalytic hydroamination of alkynes [J].

Buil, Maria L. ;

Esteruelas, Miguel A. ;

Lopez, Ana M. ;

Mateo, A. Concepcion ;

Onate, Enrique .

ORGANOMETALLICS, 2007, 26 (03) :554-565

[8] REVERSE COPE ELIMINATION-REACTIONS .1. MECHANISM AND SCOPE [J].

CIGANEK, E ;

READ, JM ;

CALABRESE, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5795-5802

[9] REVERSE COPE ELIMINATIONS - PYRROLIDINE AND PIPERIDINE N-OXIDES BY INTRAMOLECULAR ADDITION OF N,N-DISUBSTITUTED HYDROXYLAMINES TO UNACTIVATED DOUBLE-BONDS [J].

CIGANEK, E .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3007-3009

[10] REVERSE COPE ELIMINATION-REACTIONS .2. APPLICATION TO SYNTHESIS(1) [J].

CIGANEK, E .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5803-5807

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