Bronsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins

被引：224

作者：

Li, Zigang ^{[1
]}

Zhang, Junliang ^{[1
]}

Brouwer, Chad ^{[1
]}

Yang, Cai-Guang ^{[1
]}

Reich, Nicholas W. ^{[1
]}

He, Chuan ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 19期

关键词：

D O I：

10.1021/ol0610035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular addition of phenols, carboxylic acids, and protected amines to inert olefins can be catalyzed by low concentrations (1 - 5%) of triflic acid. Functional groups, such as the methoxyl substitution on aromatics, could be tolerated if the concentration of triflic acid and the reaction temperature are controlled appropriately. This reaction provides one of the simplest olefin addition methods and is an alternative to metal-catalyzed reactions.

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页码：4175 / 4178

页数：4

相关论文

共 56 条

[1] Highly selective synthesis of enamines from olefins [J].

Ahmed, M ;

Seayad, AM ;

Jackstell, R ;

Beller, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (45) :5615-5619

[2] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].

Akiyama, T ;

Morita, H ;

Itoh, J ;

Fuchibe, K .

ORGANIC LETTERS, 2005, 7 (13) :2583-2585

[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] A new asymmetric Wacker-type cyclization and tandem cyclization promoted by Pd(II)-spiro bis(isoxazoline) catalyst [J].

Arai, MA ;

Kuraishi, M ;

Arai, T ;

Sasai, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2907-2908

[5] SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES, OXANES, AND THIANES [J].

BALIAH, V ;

JEYARAMAN, R ;

CHANDRASEKARAN, L .

CHEMICAL REVIEWS, 1983, 83 (04) :379-423

[6] Advances and adventures in amination reactions of olefins and alkynes [J].

Beller, M ;

Breindl, C ;

Eichberger, M ;

Hartung, CG ;

Seayad, J ;

Thiel, OR ;

Tillack, A ;

Trauthwein, H .

SYNLETT, 2002, (10) :1579-1594

[7] Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines [J].

Bender, CF ;

Widenhoefer, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1070-1071

[8] Intramolecular hydroamination of unactived olefins with Ti(NMe2)4 as a precatalyst [J].

Bexrud, JA ;

Beard, JD ;

Leitch, DC ;

Schafer, LL .

ORGANIC LETTERS, 2005, 7 (10) :1959-1962

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

Brouwer, C ;

He, C .

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

[10]

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

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