Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions.

A facile, transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple and scalable and exhibits high functional-group tolerance.

Metal-Free Decarboxylative Alkoxylation of 2-Picolinic Acid and Its Derivatives with Cyclic Ethers: One Step Construction of C-O and C-Cl Bonds.

A new strategy for the metal-free decarboxylative alkoxylation of 2-picolinic acid and its derivatives is described. The three-component reaction of 2-picolinic acid or its derivatives, cyclic ethers, and BuOCl proceeded smoothly in the presence of a catalytic amount of p-chloranil to produce 2-alkoxylated pyridines with an ω-chlorine atom in satisfactory to excellent yields. New C-O and C-Cl bonds were generated in one step.