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Evoniuk CJ, Gomes GDP, Ly M, et al. 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. J Org Chem. 2017;82(8):4265-4278doi: 10.1021/acs.joc.7b00262.
Evoniuk, C. J., Gomes, G. D. P., Ly, M., White, F. D., & Alabugin, I. V. (2017). 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. The Journal of organic chemistry, 82(8), 4265-4278. https://doi.org/10.1021/acs.joc.7b00262
Evoniuk, Christopher J, et al. "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." The Journal of organic chemistry vol. 82,8 (2017): 4265-4278. doi: https://doi.org/10.1021/acs.joc.7b00262
Evoniuk CJ, Gomes GDP, Ly M, White FD, Alabugin IV. 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. J Org Chem. 2017 Apr 21;82(8):4265-4278. doi: 10.1021/acs.joc.7b00262. Epub 2017 Apr 03. PMID: 28357857.
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J Org Chem. 2017 Apr 21;82(8):4265-4278. doi: 10.1021/acs.joc.7b00262. Epub 2017 Apr 03.

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.

The Journal of organic chemistry

Christopher J Evoniuk, Gabriel Dos Passos Gomes, Michelle Ly, Frankie D White, Igor V Alabugin

Affiliations

  1. Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306-4390, United States.

PMID: 28357857 DOI: 10.1021/acs.joc.7b00262

Abstract

Selective addition of radicals to isonitriles can be harnessed for initiating reaction cascades designed to overcome the stereoelectronic restrictions on homoallylic ring expansion in alkyne reactions and to develop a new 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. Computational analysis of the homoallyic expansion potential energy surface reveals that the indirect 5-exo/3-exo/retro-3-exo path is faster than the direct 6-endo-trig closure, revealing the general exo-preference for the cyclization processes.

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