A simple change of solvent allows controlled and efficient switching between oxidative Heck and conjugate addition reactions on cyclic Michael acceptor substrates, catalyzed by a cationic Pd(II) catalyst system. Both reactions are ligand- and base-free and tolerant of air and moisture, and the controlled switching sheds light on some of the factors which favor one reaction over the other.

Ligand-and Base-Free Pd(II)-Catalyzed Controlled Switching Between Oxidative Heck and Conjugate Addition Reactions. -Switching between oxidative Heck and conjugated addition reaction on cyclic alkenes is achieved by a simple switch of the solvent. Both reactions are ligand-and base-free and tolerant to air and moisture. -(WALKER, S. E.; BOEHNKE, J.; GLEN, P. E.; LEVEY, S.; PATRICK, L.; JORDAN-HORE, J. A.; LEE*, A.-L.; Org. Lett. 15 (2013) 8, 1886-1889, http://dx.doi.org/10.1021/ol400539h ; Inst. Chem. Sci., Heriot-Watt Univ., Riccarton, Edinburgh EH14 4AS, UK; Eng.) -Bartels 35-082