Copper-Mediated N-Cyclopropylation of Azoles, Amides, and Sulfonamides by Cyclopropylboronic Acid

The reaction of azoles, amides, and sulfonamides in dichloroethane with readily available cyclopropylboronic acid in the presence of copper acetate and sodium carbonate afforded the N-cyclopropyl derivs. in good to excellent yields. [on SciFinder (R)]


Published in:
Journal of Organic Chemistry, 73, 16, 6441-6444
Year:
2008
Keywords:
Note:
CAN 149:223829
24-2
Alicyclic Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0022-3263
written in English.
497-19-8 (Sodium carbonate) Role: RGT (Reagent), RACT (Reactant or reagent) (optimized base; prepn. of N-cyclopropyl derivs. of azoles, amides, and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); 366-18-7 (2,2'-Bipyridine) Role: RGT (Reagent), RACT (Reactant or reagent) (optimized ligand; prepn. of N-cyclopropyl derivs. of azoles, amides, and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); 107-06-2 (1,2-Dichloroethane) Role: NUU (Other use, unclassified), USES (Uses) (optimized solvent; prepn. of N-cyclopropyl derivs. of azoles, amides, and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); 51-17-2 (Benzimidazole); 65-71-4; 85-41-6 (Phthalimide); 86-74-8 (9H-Carbazole); 86-86-2 (1-Naphthaleneacetamide); 95-14-7 (1H-Benzotriazole); 98-10-2 (Benzenesulfonamide); 120-72-9 (Indole); 626-48-2; 670-96-2 (2-Phenylimidazole); 703-80-0 (3-Acetylindole); 1006-94-6 (5-Methoxyindole); 1072-83-9 (2-Acetylpyrrole); 5401-94-5; 6146-52-7 (5-Nitroindole); 10075-50-0 (5-Bromoindole); 17630-76-1; 18063-03-1; 90719-32-7; 141215-69-2; 411235-57-9 (Cyclopropylboronic acid) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of N-cyclopropyl derivs. of azoles, amides, and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); 142-71-2 (Copper(II) acetate) Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of N-cyclopropyl derivs. of azoles, amides, and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); 7027-65-8P; 38939-62-7P; 67246-32-6P; 129716-35-4P; 401589-87-5P; 694518-58-6P; 890534-63-1P; 890534-65-3P; 925429-90-9P; 925429-96-5P; 925430-05-3P; 1021154-54-0P; 1021154-60-8P; 1042444-28-9P; 1042444-29-0P; 1042444-30-3P; 1042444-32-5P; 1042444-33-6P; 1042444-34-7P; 1042444-35-8P; 1042444-36-9P; 1042444-37-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of N-cyclopropyl derivs. of azoles, amides, and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.)
Laboratories:




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


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