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)]
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Benard, S., Neuville, L., & Zhu, J. (2008). Copper-Mediated N-Cyclopropylation of Azoles, Amides, and Sulfonamides by Cyclopropylboronic Acid. The Journal of Organic Chemistry, 73(16), 6441–6444. https://doi.org/10.1021/jo801033y
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2008
73
16
6441
6444
CAN 149:223829
24-2
Alicyclic Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
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.)
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