Palladium-catalyzed intramolecular 5-exo-dig hydroarylations of N-arylpropiolamides: thermodynamics-controlled stereoselective synthesis of 3-methyleneoxindoles.
Palladium-catalyzed intramolecular hydroarylation of N-arylpropiolamides has been developed for the stereoselective synthesis of 3-(monosubstituted methylene)oxindoles. In the presence of Pd(OAc)(2) and dppf, a variety of N-arylpropiolamides successfully underwent the intramolecular hydroarylation reaction to afford the corresponding 3-(monosubstituted-methylene)oxindoles in moderate to excellent yields. It is noteworthy that the stereoselectivity of the reaction can be controlled by varying the reaction temperature.
College of Chemistry and Materials Science, Wenzhou University, Wenzhou 325035, China.
Tao-Shan
TS
Jiang
Ri-Yuan
RY
Tang
Xing-Guo
XG
Zhang
Xin-Hua
XH
Li
Jin-Heng
JH
Li
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
D000577:Amides; D007211:Indoles; D009942:Organometallic Compounds; D000078183:Oxindoles; C008440:3-methyleneoxindole; D010165:Palladium