1.
J Org Chem
; 78(19): 9689-714, 2013 Oct 04.
Artigo
em Inglês
| MEDLINE
| ID: mdl-24090404
RESUMO
The scope of palladium-catalyzed, auxiliary-assisted direct arylation and alkylation of sp(2) and sp(3) C-H bonds of amine and carboxylic acid derivatives has been investigated. The method employs a palladium acetate catalyst, substrate, aryl, alkyl, benzyl, or allyl halide, and inorganic base in tert-amyl alcohol or water solvent at 100-140 °C. Aryl and alkyl iodides as well as benzyl and allyl bromides are competent reagents in this transformation. The picolinic acid auxiliary is used for amine γ-functionalization, and the 8-aminoquinoline auxiliary is used for carboxylic acid ß-functionalization. Some optimization of base, additives, and solvent is required for achieving best results.