Highly efficient Pd-catalyzed coupling of arenes with olefins in the presence of tert-butyl hydroperoxide as oxidant

[GRAPHICS] ArH : benzoid and non-benzoid. R = H, CH3, Ph. R-1 = Ph, Co2Et, COMe, CHO, CO2H, CN. The oxidative coupling of arenes with olefins has been performed efficiently in the presence of catalytic amounts of palladium acetate and benzoquinone (BQ) with tert-butyl hydroperoxide as the oxidant in up to 280 turnover numbers (TON). The catalytic system is especially active for the coupling of heterocycles such as furans and indole with activated olefins, The reaction is highly regio- and stereoselective, giving trans-olefins predominantly.