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.