Copper-promoted N-cyclopropylation of anilines and amines by cyclopropylboronic acid

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)]


Published in:
Chemical Communications, 46, 19, 3393-3395
Year:
2010
Publisher:
Royal Society of Chemistry
ISSN:
1359-7345
Keywords:
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:




 Record created 2010-11-25, last modified 2018-03-17


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