Different Selectivities in the Insertions into C(sp2)−H Bonds

Abstract

An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)−H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C−H positions. A bidirectional synthesis with two competing ortho-aryl C−H bonds in the selectivity-determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C−H bonds with a benzylic methyl group also showed perfect selectivity. Show more