Palladium-Catalyzed syn-Stereocontrolled Ring Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides.

A novel palladium-catalyzed ring-opening reaction of oxabicyclic alkenes with arylsulfonyl hydrazides was first developed. In this work, we provide an efficient one-pot reaction to afford the corresponding cis-2-aryl-1,2-dihydronaphthalen-1-ols and 2-aryl-naphthalenes in moderate to excellent yields (up to 95%) under an open-air condition. Various types of functional groups attached to the substrates were tolerated well in this method. Among them, the cis-1,2-configuration of product 3ag was confirmed by X-ray crystallographic analysis. In addition, a plausible mechanism for ring opening was also proposed.