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: ananthanramasamy
gmail.com
M. B. Reddy, K. Prasanth, R. Anandhan, Org. Lett., 2022, 24, 3674-3679.
DOI: 10.1021/acs.orglett.2c01296
see article for more reactions
Abstract
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.
see article for more examples
proposed mechanism
Key Words
isoindolinones, phthalimides, organocatalysis, oxygen, photochemistry
ID: J54-Y2022
