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

We report a controlled radical cyclization cascade of isoquinoline-1,3,4­(2H)-triones, 3-hydroxyisoindolin-1-ones, and phthalimides from o-alkynylated benzamides by metal-free photoredox catalyzed amidyl N-centered radical addition to the C–C triple bond using the proton-coupled electron transfer (P...

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Bibliographic Details
Published in:Organic letters 2022-05, Vol.24 (20), p.3674-3679
Main Authors: Reddy, Mandapati Bhargava, Prasanth, Kesavan, Anandhan, Ramasamy
Format: Article
Language:English
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Summary:We report a controlled radical cyclization cascade of isoquinoline-1,3,4­(2H)-triones, 3-hydroxyisoindolin-1-ones, and phthalimides from o-alkynylated benzamides by metal-free photoredox catalyzed amidyl N-centered radical addition to the C–C triple bond using the proton-coupled electron transfer (PCET) process under mild reaction conditions. A time tunable synthesis of 3-hydroxyisoindolin-1-ones and phthalimides via β-carbonyl-C­(sp3) bond cleavage was also achieved under visible light irradiation. A mechanistic rationale for the radical cyclization cascade is supported by various control and quenching experiments as well as EPR studies.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01296