Copper-promoted N-cyclopropylation of anilines and amines by cyclopropylboronic acid
2010
Abstract
Reaction of anilines, primary and secondary aliph. amines with cyclopropylboronic acid in dichloroethane in the presence of Cu(OAc)2 (1 equiv.), 2,2'-bipyridine (1 equiv.) and sodium carbonate or sodium bicarbonate (2 equiv.) under air atm. afforded the corresponding N-cyclopropyl derivs. in good to excellent yields. [on SciFinder (R)]
Details
Title
Copper-promoted N-cyclopropylation of anilines and amines by cyclopropylboronic acid
Author(s)
Benard, Sebastien ; Neuville, Luc ; Zhu, Jieping
Published in
Chemical Communications
Volume
46
Issue
19
Pages
3393-3395
Date
2010
Publisher
Royal Society of Chemistry
ISSN
1359-7345
Keywords
Alkylation; Alkylation catalysts (N-cyclopropylation; prepn. of cyclopropylamines via copper-catalyzed N-cyclopropylation of amines with cyclopropylboronic acid); Amines Role: SPN (Synthetic preparation); PREP (Preparation) (cyclopropyl; prepn. of cyclopropylamines via copper-catalyzed N-cyclopropylation of amines with cyclopropylboronic acid); cyclopropylboronic acid amine copper cyclopropylation; cyclopropylamine deriv prepn; copper cyclopropylation catalyst
Note
CAN 153:36736, 21-2, General Organic Chemistry, Centre de Recherche de Gif Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr., Journal, 1359-7345, written in English., 142-71-2 (Copper (II) acetate) Role: CAT (Catalyst use), USES (Uses) (prepn. of cyclopropylamines via copper-catalyzed N-cyclopropylation of amines with cyclopropylboronic acid); 87-62-7 (2,6-Dimethylaniline); 100-01-6 (4-Nitroaniline); 102-97-6 (N-Isopropylbenzylamine); 350-46-9 (4-Nitro-1-fluorobenzene); 496-12-8 (Isoindoline); 496-15-1 (Indoline); 765-30-0 (Aminocyclopropane); 932-96-7 (N-Methyl-4-chloroaniline); 1013-25-8 (N-(2,5-Dimethylphenyl)piperazine); 2577-90-4 ((S)-Methyl 2-amino-3-phenylpropanoate); 2780-89-4 (Methyl 6-aminohexanoate); 5699-41-2; 5961-59-1 (N-Methyl-4-methoxyaniline); 6246-48-6 (Geranylamine); 6293-83-0 (2-Iodo-4-nitroaniline); 34798-80-6 (4-Acetyl-4-phenylpiperidine); 57260-71-6 (N-Boc-piperazine); 95631-62-2 (1-Bromo-1-ethoxycyclopropane); 112275-50-0; 411235-57-9 (Cyclopropylboronic acid); 883554-87-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of cyclopropylamines via copper-catalyzed N-cyclopropylation of amines with cyclopropylboronic acid); 77278-34-3P; 112033-47-3P (N-Cyclopropyl-4-nitroaniline); 208176-50-5P (N-Cyclopropyl-N-methyl-4-chloroaniline); 743371-99-5P; 890534-58-4P; 890534-64-2P; 1000405-23-1P; 1228357-85-4P; 1228357-86-5P; 1228357-90-1P; 1228357-92-3P; 1228357-96-7P; 1228357-98-9P; 1228358-00-6P; 1228358-01-7P; 1228358-02-8P; 1228358-03-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of cyclopropylamines via copper-catalyzed N-cyclopropylation of amines with cyclopropylboronic acid)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25