Catalytic reductive N-alkylation of amines using carboxylic acids

A highly improved methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. Several examples using aliphatic, aromatic, unsaturated and fatty acids combined with primary and secondary amines are shown.

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Selective Synthesis of 1-O-Alkyl(poly)glycerol Ethers by Catalytic Reductive Alkylation of Carboxylic Acids with a Recyclable Catalytic System

ChemSusChem ◽

10.1002/cssc.201200447 ◽

2012 ◽

Vol 5 (12) ◽

pp. 2397-2409 ◽

Cited By ~ 30

Author(s):

Marc Sutter ◽

Wissam Dayoub ◽

Estelle Métay ◽

Yann Raoul ◽

Marc Lemaire

Keyword(s):

Carboxylic Acids ◽

Catalytic System ◽

Selective Synthesis ◽

Reductive Alkylation ◽

Glycerol Ethers

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ChemInform Abstract: Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation.

ChemInform ◽

10.1002/chin.201305052 ◽

2013 ◽

Vol 44 (5) ◽

pp. no-no

Author(s):

Kai-Jiong Xiao ◽

Ai-E Wang ◽

Pei-Qiang Huang

Keyword(s):

Secondary Amines ◽

Reductive Alkylation ◽

Direct Transformation ◽

Secondary Amides

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ChemInform Abstract: Highly Efficient and Eco-Friendly Synthesis of Tertiary Amines by Reductive Alkylation of Aldehydes with Secondary Amines over a Pt Nanowires Catalyst.

ChemInform ◽

10.1002/chin.201606061 ◽

2016 ◽

Vol 47 (6) ◽

pp. no-no

Author(s):

Junjie Wu ◽

Shuanglong Lu ◽

Danhua Ge ◽

Hongwei Gu

Keyword(s):

Secondary Amines ◽

Tertiary Amines ◽

Reductive Alkylation ◽

Highly Efficient ◽

Pt Nanowires

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A Reductive Alkylation Procedure Applicable to Both Solution- and Solid-Phase Syntheses of Secondary Amines

The Journal of Organic Chemistry ◽

10.1021/jo960124n ◽

1996 ◽

Vol 61 (19) ◽

pp. 6720-6722 ◽

Cited By ~ 74

Author(s):

Anna K. Szardenings ◽

Timothy S. Burkoth ◽

Gary C. Look ◽

David A. Campbell

Keyword(s):

Solid Phase ◽

Secondary Amines ◽

Reductive Alkylation

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Study of copper chromite catalysts, III. Structure and catalytic activity of copper chromite catalyst in reductive alkylation reaction

Reaction Kinetics and Catalysis Letters ◽

10.1007/bf02068341 ◽

1986 ◽

Vol 32 (2) ◽

pp. 393-398 ◽

Cited By ~ 7

Author(s):

F. Hanic ◽

G. Plesch ◽

P. Dolezel ◽

J. Ovecková

Keyword(s):

Catalytic Activity ◽

Copper Chromite ◽

Alkylation Reaction ◽

Reductive Alkylation ◽

Copper Chromite Catalyst

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Catalyst-Free One-Pot Reductive Alkylation of Primary and Secondary Amines and N,N-Dimethylation of Amino Acids Using Sodium Borohydride in 2,2,2-Trifluoroethanol

Synthesis ◽

10.1055/s-0030-1258384 ◽

2010 ◽

Vol 2011 (03) ◽

pp. 490-496 ◽

Cited By ~ 51

Author(s):

Mahmood Tajbakhsh ◽

Rahman Hosseinzadeh ◽

Heshmatollah Alinezhad ◽

Somayeh Ghahari ◽

Akbar Heydari ◽

...

Keyword(s):

Amino Acids ◽

Sodium Borohydride ◽

Secondary Amines ◽

Reductive Alkylation ◽

One Pot ◽

Catalyst Free ◽

Primary And Secondary Amines

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Synthesis of 7-substituted 3-β-D-ribofuranosyl-3H-imidazo[2,1-i]purines

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc2011069 ◽

2011 ◽

Vol 76 (8) ◽

pp. 1043-1054 ◽

Cited By ~ 2

Author(s):

Tuomas Karskela ◽

Karel D. Klika ◽

Harri Lönnberg

Keyword(s):

Secondary Amines ◽

Formyl Group ◽

Reductive Alkylation

A method for the synthesis of 7-substituted 3-β-D-ribofuranosyl-3H-imidazo[2,1-i]purines has been devised whereby compounds were prepared in a few steps from a common intermediate, 3-(2′,3′-O-isopropylidene-β-D-ribofuranosyl)-3H-imidazo[2,1-i]purine-7-carbaldehyde, obtained from the reaction of 2′,3′-O-isopropylideneadenosine with bromomalonaldehyde. The formyl group of the carbaldehyde was subsequently reductively aminated and the resulting secondary amines were then further derivatized either by acylation, lactamization or reductive alkylation.

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