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.
Tang
Dong-Jun
DJ
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, China.
Tang
Bo-Xiao
BX
Li
Jin-Heng
JH
D000813:Anilides / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D006859:Hydrogen / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007700:Kinetics; D008956:Models, Chemical; D015394:Molecular Structure; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry; D015363:Quinolones / Q000737:chemistry*; D014050:Toluene / Q000737:chemistry
D000813:Anilides; D007211:Indoles; D000078183:Oxindoles; D015363:Quinolones; C022960:2-oxindole; D014050:Toluene; D010165:Palladium; D002244:Carbon; D006859:Hydrogen