Pd(ii)-catalyzed domino C–H addition/Heck reaction for stereoselective 3-alkylideneoxindole synthesis

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%.

Graphical abstract: Pd(ii)-catalyzed domino C–H addition/Heck reaction for stereoselective 3-alkylideneoxindole synthesis

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Article information

Article type
Paper
Submitted
23 Apr 2025
Accepted
03 Jun 2025
First published
05 Jun 2025

Org. Biomol. Chem., 2025, Advance Article

Pd(II)-catalyzed domino C–H addition/Heck reaction for stereoselective 3-alkylideneoxindole synthesis

K. Hong, T. Zhang, Q. Li, X. Li, Z. Sun, G. Zhao, J. Peng and C. Chen, Org. Biomol. Chem., 2025, Advance Article , DOI: 10.1039/D5OB00666J

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