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.
Jiang
Tao-Shan
TS
College of Chemistry and Materials Science, Wenzhou University, Wenzhou 325035, China.
Tang
Ri-Yuan
RY
Zhang
Xing-Guo
XG
Li
Xin-Hua
XH
Li
Jin-Heng
JH
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