Direct reductive amination of aldehydes using lithium-arene(cat.) as reducing system. A simple one-pot procedure for the synthesis of secondary amines

被引：36

作者：

Nador, Fabiana ^{[1
]}

Moglie, Yanina ^{[1
,2
,3
]}

Ciolino, Andres ^{[4
]}

Pierini, Adriana ^{[5
]}

Dorn, Viviana ^{[1
]}

Yus, Miguel ^{[2
,3
]}

Alonso, Francisco ^{[2
,3
]}

Radivoy, Gabriel ^{[1
]}

机构：

[1] Univ Nacl Sur, Inst Quim S INQUISUR CONICET, Dept Quim, RA-8000 Bahia Blanca, Buenos Aires, Argentina

[2] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

[3] Univ Alicante, ISO, E-03080 Alicante, Spain

[4] Univ Nacl Sur, Planta Piloto Ingn Quim PLAPIQUI CONICET, Dept Ingn Quim, RA-8000 Bahia Blanca, Buenos Aires, Argentina

[5] Univ Nacl Cordoba, Inst Invest Fis Quim Cordoba INFIQC, Dept Quim Organ, RA-5000 Cordoba, Argentina

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 25期

关键词：

Lithium-arene; Aldehydes; Reductive amination; Secondary amines; DFT methods; CARBONYL-COMPOUNDS; COPPER NANOPARTICLES; SODIUM CYANOBOROHYDRIDE; ORGANIC-SYNTHESIS; ELECTRON-TRANSFER; IONIC LIQUID; KETONES; EFFICIENT; CATALYSTS; SOLVENT;

D O I：

10.1016/j.tetlet.2012.04.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple one-pot procedure for the direct reductive amination of aldehydes using lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB) or a polymer supported naphthalene as reducing system is described. The direct reductive amination of a variety of aldehydes with primary amines was achieved simply by adding a mixture of the corresponding carbonyl compound and the amine, over a solution of the lithium arenide in THF at room temperature. For most of the substrates tested the main reaction products were the secondary amines along with variable amounts of the corresponding alcohol and/or imine products. Theoretical DFT calculations have been applied in order to explain the differences in reactivity observed for aromatic substrates. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3156 / 3160

页数：5

共 19 条

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