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

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.

SUBMITTER: Li GX

PROVIDER: S-EPMC5356021 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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

Li Guo-Xing GX Morales-Rivera Christian A CA Wang Yaxin Y Gao Fang F He Gang G Liu Peng P Chen Gong G

Chemical science 20160712 10

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 functionaliza ...[more]

PMID: 28451096

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