Energy Transfer Photocatalytic Radical Rearrangement in N-Indolyl Carbonates

Milan Bera, Ho Seong Hwang, Tae-Woong Um, Soo Min Oh, Seunghoon Shin* and Eun Jin Cho*

*Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763; Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul 06974, Republic of Korea, Email: sshinhanyang.ac.kr, ejchocau.ac.kr

M. Bera, H. S. Hwang, T.-W. Um, S. M. Oh, S. Shin, E. J. Cho, Org. Lett., 2022, 24, 1774-1779.

DOI: 10.1021/acs.orglett.2c00085

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Abstract

Upon photoexcitation, homolytic N-O bond cleavage of N-indolyl carbonate in the presence of an Ir complex produced N- and O-centered radicals. The high spin density at the C3 position of indole led to radical recombination with the O-centered radical, affording valuable 3-oxyindole derivatives without decarboxylation.

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product transformations

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Key Words

indoles, photochemistry

ID: J54-Y2022