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Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

ABSTRACT: 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 ?-functionalization, and the 8-aminoquinoline auxiliary is used for carboxylic acid ?-functionalization. Some optimization of base, additives, and solvent is required for achieving best results.

SUBMITTER: Nadres ET 

PROVIDER: S-EPMC3829615 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Nadres Enrico T ET   Santos Gerson Ivan Franco GI   Shabashov Dmitry D   Daugulis Olafs O  

The Journal of organic chemistry 20130919 19

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 amin  ...[more]

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