Sequential intermolecular aminopalladation/ortho-arene C-H activation reactions of N-phenylpropiolamides with phthalimide.
A novel palladium-catalyzed intermolecular aminopalladation/C-H activation method for selectively synthesizing (E)-(2-oxindolin-3-ylidene)phthalimides has been developed. In the presence of Pd(OAc)2 and PhI(OAc)2, alkynes were difunctionalized with a phthalimide and an arene sp2 C-H bond to selectively synthesize (E)-(2-oxoindolin-3-ylidene)phthalimides, which products are of great potential pharmaceutical value products in many major therapeutic areas, such as oncology, inflammation, neurology, immunology, and endocrinology. To the best of our knowledge, the reaction serves as the first example of intermolecular aminopalladation/C-H activation reactions of alkynes.
Tang
Shi
S
Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
Peng
Peng
P
Pi
Shao-Feng
SF
Liang
Yun
Y
Wang
Nai-Xing
NX
Li
Jin-Heng
JH
D000577:Amides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010665:Phenylpropanolamine / Q000737:chemistry*; D010797:Phthalimides / Q000737:chemistry*
D000577:Amides; D010797:Phthalimides; C037431:phthalimide; D010665:Phenylpropanolamine; D010165:Palladium