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 journalArticlepeer-review

153 Scopus citations

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 - 2016

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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