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

• Published in: Journal of Organic Chemistry, vol. 73, num. 16, p. 6441-6444
• Publication date: 2008

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)]

Keywords: Amides Role: SPN (Synthetic preparation) ; PREP (Preparation) (N-cyclopropyl; prepn. of N-cyclopropyl derivs. of azoles ; amides ; and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); Alkylation (N-cyclopropylation; prepn. of N-cyclopropyl derivs. of azoles ; amides ; and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); Heterocyclic compounds Role: SPN (Synthetic preparation) ; PREP (Preparation) (nitrogen ; N-cyclopropyl; prepn. of N-cyclopropyl derivs. of azoles ; amides ; and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); Heterocyclic compounds Role: RCT (Reactant) ; RACT (Reactant or reagent) (nitrogen; prepn. of N-cyclopropyl derivs. of azoles ; amides ; and sulfonamides via copper-mediated coupling of cyclopropylboronic acid with parent compds.); Amides 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.) ; azole cyclopropylboronic acid copper acetate bipyridine N cyclopropylation; cyclopropylazole deriv prepn; amide cyclopropylboronic acid copper acetate bipyridine coupling; cyclopropylamide deriv prepn; sulfonamide cyclopropylboronic acid copper acetate bipyridine N alkylation; cyclopropylsulfonamide deriv prepn

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.)

Reference

• EPFL-ARTICLE-158069
• doi:10.1021/jo801033y

Record created on 2010-11-25, modified on 2017-05-12