Selective synthesis of 3-aryl quinolin-2(1H)-ones and 3-(1-arylmethylene)oxindoles involving a 2-fold arene C-H activation process.

A novel and selective palladium-catalyzed C-H activation protocol has been developed for the synthesis of 3-aryl quinolin-2(1H)-ones and 3-(1-arylmethylene)oxindoles with use of PivOH as the switch. In the presence of Pd(OAc)(2), AgOAc, and PivOH, a variety of N-methyl anilides reacted with arenes to afford the corresponding 3-aryl quinolin-2(1H)-ones in moderate yields, whereas the selectivity was shifted toward 3-(1-arylmethylene)oxindoles in the absence of PivOH.