穴田 仁洋

A phenanthridine synthesis based on an alkoxy-group-elimination-type S _N Ar reaction, a largely unexplored transformation in S _N Ar chemistry, was achieved.

Abstract A divergent synthetic route to indanes and benzoxepines is reported. The key to the divergence is the selection of the catalytic system. Whereas treating benzylidene malonate with a 1-alkoxyalkyl group at the ortho position with Sc(OTf)3 gave indanes via an internal redox reaction ([1,4]-hydride shift/cyclization), the simultaneous use of Sc(OTf)3 and PhCO2H afforded benzoxepines through an intramolecular nucleophilic substitution reaction.