Copper-Mediated N-Cyclopropylation of Azoles, Amides, and Sulfonamides by Cyclopropylboronic Acid
2008
Abstract
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)]
Details
Title
Copper-Mediated N-Cyclopropylation of Azoles, Amides, and Sulfonamides by Cyclopropylboronic Acid
Author(s)
Benard, Sebastien ; Neuville, Luc ; Zhu, Jieping
Published in
Journal of Organic Chemistry
Volume
73
Issue
16
Pages
6441-6444
Date
2008
ISSN
0022-3263
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
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.)
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.)
Laboratories
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