Strong Bonds Made Weak: Towards the General Utility of Amides as Synthetic Modules

被引：142

作者：

Ruider, Stefan A. ^{[1
]}

Maulide, Nuno ^{[1
]}

机构：

[1] Univ Vienna, Fak Chem, Inst Organ Chem, A-1090 Vienna, Austria

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 47期

关键词：

amides; esters; homogenous catalysis; nickel; solvolysis; CONVERSION; ESTERS; ACTIVATION; HYDROLYSIS; CLEAVAGE; ACIDS;

D O I：

10.1002/anie.201508536

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Breaking good: The amide bond is widely recognized as the strongest bond among the carboxylic acid derivatives. Therefore, the potential of amides to serve as synthetic building blocks has remained mostly untapped thus far. This Highlight describes a recent breakthrough that enables the catalytic conversion of amides into esters for the first time. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：13856 / 13858

页数：3

共 19 条

[1]

[Anonymous], 2012, ANGEW CHEM, V124, P563

[2]

[Anonymous], 2011, ANGEW CHEM, V123, P6299

[3] Chelating Carboxylic Acid Amides as Robust Relay Protecting Groups of Carboxylic Acids and their Cleavage under Mild Conditions [J].

Broehmer, Manuel C. ;

Mundinger, Stephan ;

Braese, Stefan ;

Bannwarth, Willi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6175-6177

[4] Spectroscopic studies of the electrophilic activation of amides with triflic anhydride and pyridine [J].

Charette, AB ;

Grenon, M .

CANADIAN JOURNAL OF CHEMISTRY, 2001, 79 (11) :1694-1703

[5]

Charette AB, 1998, SYNLETT, P163

[6] Efficient transamidation of primary carboxamides by in situ activation with N,N-dialkylformamide dimethyl acetals [J].

Dineen, Thomas A. ;

Zajac, Matthew A. ;

Myers, Andrew G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) :16406-16409

[7] Mild nitrosation and hydrolysis of polyfunctional amides [J].

Evans, DA ;

Carter, PH ;

Dinsmore, CJ ;

Barrow, JC ;

Katz, JL ;

Kung, DW .

TETRAHEDRON LETTERS, 1997, 38 (26) :4535-4538

[8]

Greenberg A., 2003, The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science

[9]

HANESSIA.S, 1967, TETRAHEDRON LETT, P1549

[10] Conversion of amides to esters by the nickel-catalysed activation of amide C-N bonds [J].

Hie, Liana ;

Nathel, Noah F. Fine ;

Shah, Tejas K. ;

Baker, Emma L. ;

Hong, Xin ;

Yang, Yun-Fang ;

Liu, Peng ;

Houk, K. N. ;

Garg, Neil K. .

NATURE, 2015, 524 (7563) :79-83

← 1 2 →