Iron-catalyzed aerobic oxidative amidation of tertiary amines with carboxylic acids

被引：12

作者：

Ma, Lina ^{[1
]}

Li, Yuanming ^{[1
]}

Li, Zhiping ^{[1
]}

机构：

[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

来源：

SCIENCE CHINA-CHEMISTRY | 2015年 / 58卷 / 08期

关键词：

amidation; tertiary amine; carboxylic acid; iron catalysis; oxidation; AMIDE BOND FORMATION; C-N BOND; 4-SUBSTITUTED N; N-DIALKYLANILINES; ATMOSPHERIC-PRESSURE; MOLECULAR-OXYGEN; ALCOHOLS; ALDEHYDES; CLEAVAGE; AMINOCARBONYLATION; DEALKYLATION;

D O I：

10.1007/s11426-015-5368-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An oxidative amidation of tertiary amines with carboxylic acids has been developed in the presence of FeCl3 center dot 6H(2)O as catalyst and oxygen as oxidant. A variety of tertiary amides were obtained in good to excellent yields from inexpensive and readily available reagents. The possible reaction pathways were investigated.

引用

页码：1310 / 1315

页数：6

共 50 条

[1] An iron-catalysed synthesis of amides from nitriles and amines [J].

Allen, C. Liana ;

Lapkin, Alexei A. ;

Williams, Jonathan M. J. .

TETRAHEDRON LETTERS, 2009, 50 (29) :4262-4264

[2] Aminolysis of Aryl Ester Using Tertiary Amine as Amino Donor via C-O and C-N Bond Activations [J].

Bao, Yong-Sheng ;

Zhaorigetu, Bao ;

Agula, Bao ;

Baiyin, Menghe ;

Jia, Meilin .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) :803-808

[3]

Bode JW, 2006, CURR OPIN DRUG DISC, V9, P765

[4] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].

Brennfuehrer, Anne ;

Neumann, Helfried ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133

[5] Synthesis of amides using the Ritter reaction with bismuth triflate catalysis [J].

Callens, Emmanuel ;

Burton, Andrew J. ;

Barrett, Anthony G. M. .

TETRAHEDRON LETTERS, 2006, 47 (49) :8699-8701

[6] Palladium-Catalyzed N-Demethylation/N-Acylation of Some Morphine and Tropane Alkaloids [J].

Carroll, Robert J. ;

Leisch, Hannes ;

Scocchera, Eric ;

Hudlicky, Tomas ;

Cox, D. Phillip .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (18) :2984-2992

[7] Oxidative N-dealkylation of p-cyclopropyl-N,N-dimethylaniline. A substituent effect on a radical-clock reaction rationalized by ab initio calculations on radical cation intermediates [J].

Chen, H ;

deGroot, MJ ;

Vermeulen, NPE ;

Hanzlik, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8227-8230

[8] Copper-Catalyzed Aerobic Oxidative Inert C-C and C-N Bond Cleavage: A New Strategy for the Synthesis of Tertiary Amides [J].

Chen, Xiuling ;

Chen, Tieqiao ;

Li, Qiang ;

Zhou, Yongbo ;

Han, Li-Biao ;

Yin, Shuang-Feng .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (38) :12234-12238

[9] Platinum catalysed hydrolytic amidation of unactivated nitriles [J].

Cobley, CJ ;

van den Heuvel, M ;

Abbadi, A ;

de Vries, JG .

TETRAHEDRON LETTERS, 2000, 41 (14) :2467-2470

[10]

COOLEY JH, 1989, SYNTHESIS-STUTTGART, P1

← 1 2 3 4 5 →