Pd(II)-catalyzed domino C-H addition/Heck reaction for stereoselective 3-alkylideneoxindole synthesis
Kai Hong1, Tengfei Zhang1, Qing Li1
1College of Chemistry, Chemical Engineering and Resource Utilization and Center for Innovative Research in Synthetic Chemistry and Resource Utilization, Northeast Forestry University, Harbin 150040, P. R. China. jspeng1998@nefu.edu.cn.
Abstract:
3-Alkylideneoxindole derivatives, which constitute the core structural framework of current pharmaceuticals, are widely present as bioactive components in numerous natural molecules. Herein, a Pd-catalyzed cascade synthetic method for the construction of 3-alkylideneoxindoles has been developed, and the reaction sequence comprises aryl C-H activation/intramolecular carbopalladation/Heck cross-coupling. Utilizing 10 mol% Pd(OAc)2 as the catalyst, 2 equiv. AgOAc as the oxidant, and 1 equiv. Mg(OAc)2 as the additive, a variety of N-alkyl or N-aryl anilides underwent reaction with alkenes in acetonitrile at 70 °C for 24 h to provide the corresponding (E)-3-alkylideneoxindole products with specific regio- and stereroselectivity in moderate to good yields; the best yield is 64%.
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