Transition-Metal-Free Synthesis of Carbonyl-Containing Oxindoles from N-Arylacrylamides and α-Diketones via TBHP- or Oxone-Mediated Oxidative Cleavage of C(sp(2))-C(sp(2)) Bonds.
Carbonyl-containing oxindoles can be prepared from N-arylacrylamides and α-diketones by TBHP- or oxone (KHSO5)-mediated C(sp(2))-C(sp(2)) bond cleavage and new C(sp(2))-C(sp(3)) bond formation. This methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing inexpensive and readily available reagents, thus providing a practical and efficient approach to an important class of 3-(2-oxoethyl)indolin-2-ones which are highly valued synthetic intermediates of biologically active molecules. In this transformation, alkylcarbonyl-containing oxindoles were obtained in majority when N-arylacrylamides reacted with asymmetric aliphatic/aromatic α-diketones. On the basis of the preliminary experiments, a plausible mechanism of this transformation is disclosed.
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, China.
Ming-Zhong
MZ
Zhang
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, China.
Peng-Yi
PY
Ji
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, China.
Yu-Feng
YF
Liu
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, China.
Can-Cheng
CC
Guo