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Synthesis of Functionalized Indoles via Palladium-Catalyzed Aerobic Cycloisomerization of o-Allylanilines Using Organic Redox Cocatalyst

Xiao-Shan Ning, Mei-Mei Wang, Jian-Ping Qu*, Yan-Biao Kang*

*School of Chemistry and Molecular Engineering, 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.-S. Ning, M.-M. Wang, J.-P. Qu, Y.-B. Kang, J. Org. Chem., 2018, 83, 13523-13529.

DOI: 10.1021/acs.joc.8b01999 (free Supporting Information)


Abstract

Using a scalable and practical synthesis of functionalized indoles via Pd-tBuONO cocatalyzed cycloisomerization of o-allylanilines in the presence of oxygen as a terminal oxidant, a series of substituted indoles were prepared in good yields. The method avoids hazardous oxidants, heavy-metal cocatalysts, and high boiling point solvents such as DMF and DMSO.

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Key Words

indoles, oxygen


ID: J42-Y2018