Palladium-catalyzed C-H functionalization of N-arylpropiolamides with aryliodonium salts: selective synthesis of 3-(1-arylmethylene)oxindoles.
A selective and efficient method for the synthesis of 3-(1-arylmethylene)oxindoles by palladium-catalyzed C-H functionalization of anilides with aryliodonium salts has been developed. In the presence of Pd(OAc)2 and Et3N, a variety of anilides underwent the reaction with aryliodonium salts to afford the corresponding 3-(1-arylmethylene)oxindoles in moderate to good yields. It is noteworthy that the reaction can be conducted providing moderate yields even without bases. The mechanism of the reaction was also discussed.
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, China.
Shi
S
Tang
Peng
P
Peng
Ping
P
Zhong
Jin-Heng
JH
Li
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D017613:Iodine Compounds / Q000737:chemistry*; D008697:Methane / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*; D012492:Salts / Q000737:chemistry
D000577:Amides; D007211:Indoles; D017613:Iodine Compounds; D000078183:Oxindoles; D012492:Salts; C022960:2-oxindole; D010165:Palladium; D002244:Carbon; D006859:Hydrogen; D008697:Methane