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Controlled Photochemical Synthesis of Substituted Isoquinoline-1,3,4(2H)-triones, 3-Hydroxyisoindolin-1-ones, and Phthalimides via Amidyl Radical Cyclization Cascade

Mandapati Bhargava Reddy, Kesavan Prasanth and Ramasamy Anandhan*

*Department of Organic Chemistry, University of Madras, Chennai-600025, Tamilnadu, India, Email:

M. B. Reddy, K. Prasanth, R. Anandhan, Org. Lett., 2022, 24, 3674-3679.

DOI: 10.1021/acs.orglett.2c01296

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A metal-free photoredox catalyzed amidyl N-centered radical addition to the C-C triple bond of o-alkynylated benzamides provides isoquinoline-1,3,4(2H)-triones, 3-hydroxyisoindolin-1-ones, and phthalimides via a proton-coupled electron transfer (PCET) process under mild reaction conditions.

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proposed mechanism

Key Words

isoindolinones, phthalimides, organocatalysis, oxygen, photochemistry

ID: J54-Y2022