Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

Trevor C. Sherwood, Hai Yun Xiao, Roshan G. Bhaskar, Eric M. Simmons, Serge Zaretsky, Martin P. Rauch, Robert R. Knowles, T. G.Murali Dhar

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

Original languageEnglish (US)
Pages (from-to)8360-8379
Number of pages20
JournalJournal of Organic Chemistry
Volume84
Issue number13
DOIs
StatePublished - Jul 5 2019

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Sherwood, T. C., Xiao, H. Y., Bhaskar, R. G., Simmons, E. M., Zaretsky, S., Rauch, M. P., Knowles, R. R., & Dhar, T. G. M. (2019). Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light. Journal of Organic Chemistry, 84(13), 8360-8379. https://doi.org/10.1021/acs.joc.9b00432