Fast Pd- and Pd/Cu-Catalyzed Direct C-H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters.

Emilien Demory (1) , Daniel Farran (2) , Benoit Baptiste (2) , Pierre y Chavant (1) , Véronique Blandin (1)

1 DCM - SeRCO - Département de Chimie Moléculaire - Synthèse Et Réactivité en Chimie Organique
2 DCM - Département de Chimie Moléculaire

Cocatalysis by pivalic acid or copper bromide allows a very fast, clean, and high-yielding palladium-catalyzed coupling of a large array of aryl, thienyl, and pyridyl halides with cyclic nitrones, including DMPO. The study of the reaction conditions, scope, and mechanism is presented. Applied to the chiral nitrone MiPNO, this transformation provides a straightforward access to enantiopure α-methyl α-arylglycine esters.

Domaines: Chimie organique

Emilien Demory, Daniel Farran, Benoit Baptiste, Pierre y Chavant, Véronique Blandin. Fast Pd- and Pd/Cu-Catalyzed Direct C-H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters.. Journal of Organic Chemistry, 2012, 77 (18), pp.7901-12. ⟨10.1021/jo301114k⟩. ⟨hal-00748949⟩