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Copper-Catalyzed C(sp3)-OH Cleavage with Concomitant C-C Coupling: Synthesis of 3-Substituted Isoindolinones

H. Surya Prakash Rao* and A. Veera Bhadra Rao

*Department of Chemistry, Pondicherry University, Pondicherry 605 014, India, Email:

H. S. P. Rao, A. V. B. Rao, J. Org. Chem., 2015, 80, 1506-1516.

DOI: 10.1021/jo502446k

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Copper(II) trifluoromethanesulfonate efficiently catalyzes the C-C coupling of 3-hydoxyisoindolinones with various aryl-, heteroaryl-, and alkenylboronic acids to furnish C(3)-substituted isoindolinones in 1,2-dicholoroethane (DCE) at reflux. The photolabile 2-nitrobenzyl protecting group is most appropriate for promotion of the coupling reaction and for deprotection.

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Key Words


ID: J42-Y2015