Ruthenium-catalyzed oxidative cyanation of tertiary amines with hydrogen peroxide and sodium cyanide

被引：244

作者：

Murahashi, SI ^{[1
]}

Komiya, N ^{[1
]}

Terai, H ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Toyonaka, Osaka 5608531, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 42期

关键词：

arnines; cyanides; hydrogen peroxide; oxidation; ruthenium;

D O I：

10.1002/anie.200501496

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Versatile intermediates for the synthesis of N-aryl-α-amino acids and N,N-disubstituted 1,2-diamines can now be synthesized with high efficiency by the ruthenium-catalyzed oxidative cyanation of tertiary amines. The use of hydrogen peroxide as an oxidant in the presence of NaCN/AcOH or HCN provides the corresponding α-aminonitriles (see reaction). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6931 / 6933

页数：3

共 55 条

[1]

ALLEN CFH, 1943, ORG SYNTH, V2, P498

[2]

Arends I. W. C. E., 1997, ANGEW CHEM, V109, P1190

[3] Recent developments in selective catalytic epoxidations with H2O2 [J].

Arends, IWCE ;

Sheldon, RA .

TOPICS IN CATALYSIS, 2002, 19 (01) :133-141

[4] Oxidative transformations of organic compounds mediated by redox molecular sieves [J].

Arends, IWCE ;

Sheldon, RA ;

Wallau, M ;

Schuchardt, U .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (11) :1144-1163

[5] SELECTIVE OXIDATION OF ALCOHOLS BY A H2O2-RUCL3 SYSTEM UNDER PHASE-TRANSFER CONDITIONS [J].

BARAK, G ;

DAKKA, J ;

SASSON, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3553-3555

[6]

Barrett G.C., 1985, CHEM BIOCH AMINO ACI, P246

[7] THE SELECTIVE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS - GIF CHEMISTRY [J].

BARTON, DHR ;

DOLLER, D .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) :504-512

[8] MONOOXYGENASE-LIKE OXIDATION OF HYDROCARBONS BY H2O2 CATALYZED BY MANGANESE PORPHYRINS AND IMIDAZOLE - SELECTION OF THE BEST CATALYTIC-SYSTEM AND NATURE OF THE ACTIVE OXYGEN SPECIES [J].

BATTIONI, P ;

RENAUD, JP ;

BARTOLI, JF ;

REINAARTILES, M ;

FORT, M ;

MANSUY, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8462-8470

[9] METAL CATALYSIS IN OXIDATION BY PEROXIDES .25. MOLYBDENUM-CATALYZED AND TUNGSTEN-CATALYZED OXIDATIONS OF ALCOHOLS BY DILUTED HYDROGEN-PEROXIDE UNDER PHASE-TRANSFER CONDITIONS [J].

BORTOLINI, O ;

CONTE, V ;

DIFURIA, F ;

MODENA, G .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2661-2663

[10]

DANGEL AC, 1993, J CHEM SOC DA, P2683

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