TEMPO Oxoammonium Salt-Mediated Dehydrogenative Povarov/Oxidation Tandem Reaction of N-Alkyl Anilines

被引：193

作者：

Richter, Heinrich ^{[1
]}

Mancheno, Olga Garcia ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 22期

关键词：

COUPLING REACTIONS; IRON; QUINOLINE; ALDEHYDES; EFFICIENT; PROGRESS; AMINES; METAL; ACID;

D O I：

10.1021/ol202552y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a variety of substituted quinolines from N-alkyl anilines by a one-pot dehydrogenative Povarov/oxidation tandem reaction with mono- and 1,2-disubstituted aryl and alkyl olefins was developed. A simple protocol using cheap and benign iron(111)chloride as the Lewis acid catalyst and a TEMPO oxoammonium salt as a nontoxic, mild, efficient oxidant is reported.

引用

页码：6066 / 6069

页数：4

共 39 条

[1]

Bobbitt J.M., 2010, ORG REACT, V74, P103, DOI [10.1002/0471264180.or074.02, DOI 10.1002/0471264180.OR074.02]

[2] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[3] Iron(III)-Catalyzed and Air-Mediated Tandem Reaction of Aldehydes, Alkynes and Amines: An Efficient Approach to Substituted Quinolines [J].

Cao, Ke ;

Zhang, Fu-Min ;

Tu, Yong-Qiang ;

Zhuo, Xiao-Tao ;

Fan, Chun-An .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (26) :6332-6334

[4] Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes [J].

Correa, Arkaitz ;

Mancheno, Olga Garcia ;

Bolm, Carsten .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) :1108-1117

[5] Intramolecular Imino Diels-Alder Reaction: Progress toward the Synthesis of Uncialamycin [J].

Desrat, Sandy ;

van de Weghe, Pierre .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) :6728-6734

[6]

Eicher T., 2003, The Chemistry of Heterocycles, P52, DOI [10.1002/352760183X.ch5a, DOI 10.1002/352760183X]

[7] Sustainable metal catalysis with iron: From rust to a rising star? [J].

Enthaler, Stephan ;

Junge, Kathrin ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3317-3321

[8] From Oblivion into the Limelight: Iron (Domino) Catalysis [J].

Fuerstner, Alois .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) :1364-1367

[9] Iron-Catalyzed Oxidative Mono- and Bis-Phosphonation of N,N-Dialkylanilines [J].

Han, Wei ;

Mayer, Peter ;

Ofial, Armin R. .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1667-1676

[10] Iron-catalyzed dehydrogenative phosphonation of N,N-dimethylanilines [J].

Han, Wei ;

Ofial, Armin R. .

CHEMICAL COMMUNICATIONS, 2009, (40) :6023-6025

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