A ligand-free approach to substituted (Z)-3-methyleneisoindolin-1-ones via Cu (I) catalyzed regio- and stereo-selective assembly of 2-iodo benzamide and terminal alkyne

Abstract

A ligand-free and cost-effective synthesis of substituted 3-methyleneisoindolin -1-ones from 2-iodobenzamide and terminal alkyne under copper (I)-catalyzed condition was accomplished. The reaction affords excellent yield of the product at a relatively lower temperature and exclusive Z-selectivity was observed in the title compound. By varying the substitution pattern on N-atom of benzamide or aromatic core of the alkyne system, a large array of substituted 3-methyleneisoindolin-1-one derivatives could be accessed employing this method.

Graphical Abstract

Keywords:

• Domino reaction
• ligand free
• 3-methyleneisoindolin-1-one
• regio- and stereo-selective cross coupling
• Z-selectivity

Acknowledgments

We sincerely thank the Sophisticated Analytical Instruments Facility (SAIF), Indian Institute of Engineering Science and Technology (IIEST) Shibpur for the XRD facility.

Additional information

Funding

The present work is financially supported from DST-SERB, New Delhi [SB/S1/OC-15/2014] and CSIR, New Delhi [02(0270)/16/EMR-II].