Highly Selective Cross-Coupling/Cyclization Reactions Involving Alkenylphenols

We initiates a project that aims to realize the cross-coupling of alkenyl phenols with another partner,such as 2-aminophenols,phenols,2-（1H-indol-2-yl）phenols,or benzyl alcohols.More details are showed as following:1.A method for the controllable synthesis of 3-arylbenzomorpholine and 2-aryl-benzomorpholine cycloadducts via cross-coupling/annulation between electron-rich 2-aminophenols and 4-vinylphenols is presented.Molecular oxygen was successfully used in the reaction as the terminal oxidant,Rose Bengal as photocatalyst and the complete inversion of chemoselectivity is achieved by the adjustment of the solvents and bases at room temperature.2.A Cu catalyzed oxidative cross-coupling reaction of alkenylphenols and other coupling partners is developed.The method proceeds under benign conditions,using O₂ in air as the oxidant at room temperature.More specifically,a regioselective oxidative cross-coupling for the direct construction of heterodimer 8-5′or 8-O-4′neolignan analogs is demonstrated.3.A photocatalyzed oxidative radical cross-coupling/cyclization between alkenylphenols and 2-（1H-indol-2-yl）phenols is presented.Various dihydrobenzoxepino indole polycyclic skeletons can be obtained at room temperature in a highly selective manner.4.A photoacid catalyzed formation of a carbocation from readily available benzyl alcohols under visible light at room temperature is demonstrated.The protocol enables simple benzyl alcohols and alkenylphenols as raw materials for synthesizing dihydroindene and chromane skeletons.