Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine

Guo Xing Li, Christian A. Morales-Rivera, Yaxin Wang, Fang Gao, Gang He, Peng Liu, Gong Chen

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Abstract

A photoredox-mediated Minisci C-H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)3]Cl2 as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, and offers a broadly applicable method for late-stage functionalization of complex substrates. Mechanistic experiments and computational studies suggest that an intramolecularly stabilized ortho-iodobenzoyloxy radical intermediate might play a key role in this reaction system.

Original languageEnglish (US)
Pages (from-to)6407-6412
Number of pages6
JournalChemical Science
Volume7
Issue number10
DOIs
StatePublished - Jan 1 2016

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Li, G. X., Morales-Rivera, C. A., Wang, Y., Gao, F., He, G., Liu, P., & Chen, G. (2016). Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine. Chemical Science, 7(10), 6407-6412. https://doi.org/10.1039/c6sc02653b