Charles G. Clark

New aryl/heteroaryl CN bond cross-coupling reactions via arylboronic acid/cupric acetate arylation

Abstract A new aryl/heteroaryl CN bond cross-coupling reaction via the arylboronic acid/cupric acetate arylation of NH containing heteroarenes has been discovered. This new methodology is mild, proceeds at room temperature exposed to air, and works for many heteroarenes and arylboronic acids providing good yields of N-arylated heteroarenes.

Copper-catalyzed general CN and CO bond cross-coupling with arylboronic acid

General catalytic Cu(OAc)2/TEMPO in air or Cu(OAc)2/O2 systems for the CN and CO cross-coupling reactions with arylboronic acid have been discovered. N- and O-vinylation have also been demonstrated.

α-Nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid

Abstract Heteroarylcarboxamides containing α-nitrogens undergo copper-promoted N -phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air . Arylboronic acid can substitute for phenyl trimethylsiloxane as the organometalloid. The α-heteroatom chelating effect is in the decreasing order of N>O, S. This discovery opens up the possibility of using other α-nitrogen functional groups to direct the N -arylation of peptides and simple amides under conditions as mild as that of amide bond formation.