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Endo/Exo-Controllable Photocyclization by EnT-SET-Switch

Xian-Peng Cai, Bin-Hong Han, Fu-Tong Cen, Jian-Ping Qu* and Yan-Biao Kang*

*Nanjing Tech University, Nanjing 211816; University of Science and Technology of China, Hefei, Anhui 230026, China, Email: ias_jpqunjtech.edu.cn, ybkangustc.edu.cn

X.-P. Cai, B.-H. Han, F.-T. Cen, J.-P. Qu, Y.-B. Kang, Org. Lett., 2023, 25, 2863-2867.

DOI: 10.1021/acs.orglett.3c00837



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Abstract

CBZ6, a redox-neutral non-donor-acceptor-type organo-photocatalyst, has a strong reductive potential and mediates both single-electron transfer and triplet energy transfer processes. The intramolecular hydroarylation of acrylamides provides both oxindoles as 5-exo-trig and dihydroquinolinones as 6-endo-trig cyclization products regiospecfically under mild conditions depending on the solvent used.

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proposed mechanism


CBZ6



Key Words

oxindoles, photochemistry, organocatalysis


ID: J54-Y2023