Photolability of per-arylated butadienes: en route to dihydronaphthalenes

J Org Chem. 2014 Dec 5;79(23):11787-91. doi: 10.1021/jo502293q. Epub 2014 Nov 17.

Abstract

Arylated butadienes were prepared employing transition-metal coupling techniques and characterized via UV/vis spectroscopy and X-ray crystal structure analysis. Identification of byproducts led to a photochemical route toward novel multiarylated dihydronaphthalenes. Arylbutadiene-dihydronaphthalene cyclization occurs in solution and in the solid state. Upon substitution of hexaphenylbutadiene, absorption is red-shifted and stability under ambient light is even more reduced.