Oxidative Arylation of Isochroman

We report the use of a previously intractable nucleophile,
anisole,
in an oxidative “cross-dehydrogenative coupling” (CDC)
reaction with the cyclic ether isochroman, as well as derivatives
of both components. Metal catalysis was required for the reaction
to proceed efficiently, and the reaction is highly sensitive to modification
of either coupling partner but is able to produce a range of novel
compounds via what is a synthetic alternative to
the traditional oxa-Pictet–Spengler reaction.