Ruthenium-Catalyzed Transfer Hydrogenation of Nitriles: Reduction and Subsequent N-Monoalkylation to Secondary Amines

被引：42

作者：

Werkmeister, Svenja ^{[1
]}

Bornschein, Christoph ^{[1
]}

Junge, Kathrin ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 18期

关键词：

Amines; Nitriles; Alkylation; Ruthenium; Transfer hydrogenation; ASYMMETRIC HYDROGENATION; TRANSITION-METAL; ENANTIOSELECTIVE HYDROGENATION; CARBONYL-COMPOUNDS; TERTIARY-AMINES; AMINATION; ALKYLATION; ACID; EFFICIENT; ALDEHYDES;

D O I：

10.1002/ejoc.201300151

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective synthesis of amines continues to be of importance because of their application in the bulk and fine chemical industries. Herein, domino ruthenium-catalyzed transfer hydrogenation of nitriles with subsequent N-monoalkylation by using alcohols is described. With this novel approach, various nitriles were reductively N-monoalkylated in excellent yields.

引用

页码：3671 / 3674

页数：4

共 84 条

[1] A review on the use of sodium triacetoxyborohydride in the reductive amination of ketones and aldehydes [J].

Abdel-Magid, Ahmed F. ;

Mehrman, Steven J. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (05) :971-1031

[2] General zinc-catalyzed intermolecular hydroamination of terminal alkynes [J].

Alex, Karolin ;

Tillack, Annegret ;

Schwarz, Nicolle ;

Beller, Matthias .

CHEMSUSCHEM, 2008, 1 (04) :333-338

[3] The Catalytic Amination of Alcohols [J].

Baehn, Sebastian ;

Imm, Sebastian ;

Neubert, Lorenz ;

Zhang, Min ;

Neumann, Helfried ;

Beller, Matthias .

CHEMCATCHEM, 2011, 3 (12) :1853-1864

[4] Ruthenium-catalyzed Selective Monoamination of Vicinal Diols [J].

Baehn, Sebastian ;

Tillack, Annegret ;

Imm, Sebastian ;

Mevius, Kathleen ;

Michalik, Dirk ;

Hollmann, Dirk ;

Neubert, Lorenz ;

Beller, Matthias .

CHEMSUSCHEM, 2009, 2 (06) :551-557

[5] Iridium-Catalyzed Asymmetric Hydrogenation of Imines [J].

Baeza, Alejandro ;

Pfaltz, Andreas .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (13) :4003-4009

[6] CATALYTIC SYNTHESIS OF HIGHER ALIPHATIC-AMINES FROM THE CORRESPONDING ALCOHOLS [J].

BAIKER, A ;

KIJENSKI, J .

CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 1985, 27 (04) :653-697

[7] Direct reductive amination of carbonyl compounds with primary/secondary amines using recyclable water-soluble FeII/EDTA complex as catalyst [J].

Bhor, Malhari D. ;

Bhanushali, Mayur J. ;

Nandurkar, Nam S. ;

Bhanage, Bhalchandra M. .

TETRAHEDRON LETTERS, 2008, 49 (06) :965-969

[8] An efficient method for the selective iridium-catalyzed monoalkylation of (hetero)aromatic amines with primary alcohols [J].

Blank, Benoit ;

Madalska, Martyna ;

Kempe, Rhett .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) :749-758

[9] Selective hydrogenation for fine chemicals: Recent trends and new developments [J].

Blaser, HU ;

Malan, C ;

Pugin, B ;

Spindler, F ;

Steiner, H ;

Studer, M .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151

[10] CHIRAL BUILDING-BLOCKS FOR THE SYNTHESIS OF N-CONTAINING NATURAL-PRODUCTS .1. ENANTIOMERICALLY PURE OXYGENATED 1-PHENYLETHYLAMINES FROM SUBSTITUTED ACETOPHENONES - BY REDUCTIVE AMINATION AND REGIOSPECIFIC BENZYLIC CLEAVAGE [J].

BRINGMANN, G ;

GEISLER, JP .

TETRAHEDRON LETTERS, 1989, 30 (03) :317-320

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