Replacement of Stoichiometric DDQ with a Low Potential<i>o</i>-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates

Abstract

A transition-metal/quinone complex, [Ru(phd)₃]²⁺ (phd = 1,10-phenanthroline-5,6-dione), is shown to be effective for aerobic dehydrogenation of 3° indolines to the corresponding indoles. The results show how low potential quinones may be tailored to provide a catalytic alternative to stoichiometric DDQ, due to their ability to mediate efficient substrate dehydrogenation while also being compatible with facile reoxidation by O₂. The utility of the method is demonstrated in the synthesis of key intermediates to pharmaceutically important molecules.