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Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals

Christopher J. Evoniuk, Gabriel dos Passos Gomes, Michelle Ly, Frankie D. White and Igor V. Alabugin*

*Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, United States, Email:

C. J. Evoniuk, G. dos Passos Gomes, M. Ly, F. D. White, I. V. Alabugin, J. Org. Chem., 2017, 82, 4265-4278.

DOI: 10.1021/acs.joc.7b00262

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Selective addition of radicals to isonitriles enables a general route for the preparation of N-heteroaromatics. This method utilizes alkenes as synthetic equivalents of alkynes by coupling homoallylic ring expansion to yield the formal 6-endo products with aromatization via stereoelectronically assisted C-C bond scission.

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Key Words

Quinolines, Manganese Compounds

ID: J42-Y2017