Ruthenium-Catalyzed Tertiary Amine Formation from Nitroarenes and Alcohols

被引：79

作者：

Feng, Chao ^{[1
]}

Liu, Yong ^{[1
]}

Peng, Shengming ^{[1
]}

Shuai, Qi ^{[2
]}

Deng, Guojun ^{[1
]}

Li, Chao-Jun ^{[2
]}

机构：

[1] Xiangtan Univ, Key Lab Environm Friendly Chem & Applicat, Minist Educ, Coll Chem, Xiangtan 411105, Peoples R China

[2] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; C-H BONDS; N-ALKYLATION; ARYL IODIDES; AMINATION; SULFONAMIDES; LIBERATION; ACTIVATION; VERSATILE; STRATEGY;

D O I：

10.1021/ol1020527

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly selective ruthenium-catalyzed C-N bond formation was developed by using the hydrogen-borrowing strategy. Various tertiary amines were obtained efficiently from nitroarenes and primary alcohols. The reaction tolerates a wide range of functionalities. A tentative mechanism was proposed for this direct amination reaction of alcohols with nitroarenes.

引用

页码：4888 / 4891

页数：4

共 62 条

[1] A diaminochlorophosphine for palladium-catalyzed arylations of amines and ketones [J].

Ackermann, Lutz ;

Spatz, Julia H. ;

Gschrei, Christian J. ;

Born, Robert ;

Althammer, Andreas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7627-7630

[2] Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature [J].

Al-Zoubi, Raed M. ;

Marion, Olivier ;

Hall, Dennis G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2876-2879

[3]

[Anonymous], 2002, HDB ORGANOPALLADIUM

[4] Selective Ruthenium-Catalyzed N-Alkylation of Indoles by Using Alcohols [J].

Baehn, Sebastian ;

Imm, Sebastian ;

Mevius, Kathleen ;

Neubert, Lorenz ;

Tillack, Annegret ;

Williams, Jonathan M. J. ;

Beller, Matthias .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (12) :3590-3593

[5] Synthesis of Selectively Mono-N-Arylated Aliphatic Diamines via Iridium-Catalyzed Amine Alkylation [J].

Blank, Benoit ;

Michlik, Stefan ;

Kempe, Rhett .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) :2903-2911

[6] The thermal and boron-catalysed direct amide formation reactions: mechanistically understudied yet important processes [J].

Charville, Hayley ;

Jackson, David ;

Hodges, George ;

Whiting, Andrew .

CHEMICAL COMMUNICATIONS, 2010, 46 (11) :1813-1823

[7]

Chen B., 2010, NATURE, V465, P1027

[8] Catalytic C-H amination: recent progress and future directions [J].

Collet, Florence ;

Dodd, Robert H. ;

Dauban, Philippe .

CHEMICAL COMMUNICATIONS, 2009, (34) :5061-5074

[9] Chemoselective hydrogenation of nitro compounds with supported gold catalysts [J].

Corma, Avelino ;

Serna, Pedro .

SCIENCE, 2006, 313 (5785) :332-334

[10] Copper-Catalyzed N-Alkylation of Sulfonamides with Benzylic Alcohols: Catalysis and Mechanistic Studies [J].

Cui, Xinjiang ;

Shi, Feng ;

Tse, Man Kin ;

Goerdes, Dirk ;

Thurow, Kerstin ;

Beller, Matthias ;

Deng, Youquan .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) :2949-2958

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