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

Research output: Contribution to journalArticle

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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 ]Cl 2 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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Boronic Acids
Alkylation
Iodine
Substrates
Photocatalysts
Oxidants
Functional groups
Experiments
tris(2,2'-bipyridine)ruthenium II

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
Li, Guo Xing ; Morales-Rivera, Christian A. ; Wang, Yaxin ; Gao, Fang ; He, Gang ; Liu, Peng ; Chen, Gong. / Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine. In: Chemical Science. 2016 ; Vol. 7, No. 10. pp. 6407-6412.
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Li, GX, Morales-Rivera, CA, 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, vol. 7, no. 10, pp. 6407-6412. https://doi.org/10.1039/c6sc02653b

Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine. / Li, Guo Xing; Morales-Rivera, Christian A.; Wang, Yaxin; Gao, Fang; He, Gang; Liu, Peng; Chen, Gong.

In: Chemical Science, Vol. 7, No. 10, 01.01.2016, p. 6407-6412.

Research output: Contribution to journalArticle

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AU - He, Gang

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