Mild Oxidative One-Carbon Homologation of Aldehyde to Amide
2005
Abstract
One-carbon homologation of aldehyde into amide is realized in one-pot by its reaction with potassium alpha -(p-methoxyphenyl)-alpha -isocyano acetic acid and hydrochloride salt of dimethylamine in toluene at room temp. followed by acidic workup. In this multicomponent reaction, alpha -p-methoxyphenyl-alpha -isocyano acetic acid served as donor of the CONH2 function to aldehyde, while the dimethylamine acted as a shuttle mol. to initiate/terminate the sequence and to mediate the internal redox process of one of the three-component adducts. Ready accessibility, nominal cost of the reagents, and mild conditions are attractive features of the present method. [on SciFinder (R)]
Details
Title
Mild Oxidative One-Carbon Homologation of Aldehyde to Amide
Author(s)
Bonne, Damien ; Dekhane, Mouloud ; Zhu, Jieping
Published in
Journal of the American Chemical Society
Volume
127
Issue
19
Pages
6926-6927
Date
2005
ISSN
0002-7863
Keywords
Homologation; Oxidation (prepn. of amides via mild; oxidative one-carbon homologation using aldehyde; amine salt; and alpha -isocyano phenylacetate as reactants); Aldehydes Role: RCT (Reactant); RACT (Reactant or reagent) (prepn. of amides via mild; oxidative one-carbon homologation using aldehyde; amine salt; and alpha -isocyano phenylacetate as reactants); Amides Role: SPN (Synthetic preparation); PREP (Preparation) (prepn. of amides via mild; oxidative one-carbon homologation using aldehyde; amine salt; and alpha -isocyano phenylacetate as reactants); mild oxidative one carbon homologation aldehyde amide prepn; aldehyde homologation oxidn amine salt isocyano phenylacetate
Note
CAN 143:59309
21-2
General Organic Chemistry
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
66-99-9 (2-Naphthaldehyde); 78-84-2 (2-Methylpropanal); 99-61-6 (3-Nitrobenzaldehyde); 108-94-1 (Cyclohexanone); 111-71-7 (Heptanal); 120-92-3 (Cyclopentanone); 500-22-1 (3-Pyridinecarboxaldehyde); 591-31-1; 3132-99-8 (3-Bromobenzaldehyde); 4894-75-1; 5949-05-3 ((-)-Citronellal); 74511-27-6 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano methoxyphenylacetate salt as reactants); 103-81-1P (Benzeneacetamide); 541-46-8P; 629-01-6P (Octanamide); 1122-56-1P (Cyclohexanecarboxamide); 3217-94-5P (Cyclopentanecarboxamide); 3724-16-1P (3-Pyridineacetamide); 5247-25-6P; 18463-71-3P (3-Methoxyphenyl acetamide); 36660-46-5P (2-Naphthaleneacetamide); 60312-83-6P (3-Bromophenyl acetamide); 853945-71-8P; 853945-72-9P; 853945-73-0P; 853945-74-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano methoxyphenylacetate salt as reactants); 51579-95-4P; 853945-66-1P Role: BYP (Byproduct), PREP (Preparation) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano phenylacetate as reactants); 506-59-2 (Dimethylamine hydrochloride); 2043-61-0 (Cyclohexanecarboxaldehyde); 817636-51-4; 853945-60-5; 853945-62-7; 853945-63-8; 853945-64-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano phenylacetate as reactants); 853945-61-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano phenylacetate as reactants); 1503-87-3P (Cyclohexaneacetamide) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of amides via mild, oxidative one-carbon homologation using cyclohexanecarboxaldehyde, amine salt, and alpha -isocyano phenylacetate as reactants); 100-52-7 (Benzaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using oxoalkylimino amide as synthetic intermediate); 853945-65-0P; 853945-67-2P; 853945-68-3P; 853945-69-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using oxoalkylimino amide as synthetic intermediate); 14389-69-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of benzylidene Ph oxazolone and study of its formation as intermediate in oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano methoxyphenylacetate salt as reactants); 13226-99-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of alpha -isocyano phenylacetate using amino ester hydrochloride as starting material); 143323-39-1P; 853945-70-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of alpha -isocyano phenylacetate using formyl Ph glycine ester as synthetic intermediate)
21-2
General Organic Chemistry
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
66-99-9 (2-Naphthaldehyde); 78-84-2 (2-Methylpropanal); 99-61-6 (3-Nitrobenzaldehyde); 108-94-1 (Cyclohexanone); 111-71-7 (Heptanal); 120-92-3 (Cyclopentanone); 500-22-1 (3-Pyridinecarboxaldehyde); 591-31-1; 3132-99-8 (3-Bromobenzaldehyde); 4894-75-1; 5949-05-3 ((-)-Citronellal); 74511-27-6 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano methoxyphenylacetate salt as reactants); 103-81-1P (Benzeneacetamide); 541-46-8P; 629-01-6P (Octanamide); 1122-56-1P (Cyclohexanecarboxamide); 3217-94-5P (Cyclopentanecarboxamide); 3724-16-1P (3-Pyridineacetamide); 5247-25-6P; 18463-71-3P (3-Methoxyphenyl acetamide); 36660-46-5P (2-Naphthaleneacetamide); 60312-83-6P (3-Bromophenyl acetamide); 853945-71-8P; 853945-72-9P; 853945-73-0P; 853945-74-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano methoxyphenylacetate salt as reactants); 51579-95-4P; 853945-66-1P Role: BYP (Byproduct), PREP (Preparation) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano phenylacetate as reactants); 506-59-2 (Dimethylamine hydrochloride); 2043-61-0 (Cyclohexanecarboxaldehyde); 817636-51-4; 853945-60-5; 853945-62-7; 853945-63-8; 853945-64-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano phenylacetate as reactants); 853945-61-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano phenylacetate as reactants); 1503-87-3P (Cyclohexaneacetamide) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of amides via mild, oxidative one-carbon homologation using cyclohexanecarboxaldehyde, amine salt, and alpha -isocyano phenylacetate as reactants); 100-52-7 (Benzaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using oxoalkylimino amide as synthetic intermediate); 853945-65-0P; 853945-67-2P; 853945-68-3P; 853945-69-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of amides via mild, oxidative one-carbon homologation using oxoalkylimino amide as synthetic intermediate); 14389-69-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of benzylidene Ph oxazolone and study of its formation as intermediate in oxidative one-carbon homologation using aldehyde, amine salt, and alpha -isocyano methoxyphenylacetate salt as reactants); 13226-99-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of alpha -isocyano phenylacetate using amino ester hydrochloride as starting material); 143323-39-1P; 853945-70-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of alpha -isocyano phenylacetate using formyl Ph glycine ester as synthetic intermediate)
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Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
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Published
Peer-reviewed publications
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Record creation date
2010-11-25