PtBr2-catalyzed consecutive enyne metathesis-aromatization of 1-(1-methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:: Dual role of the Pt catalyst

1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr2 acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the eryne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.