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

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 u...

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Published in:Chemical science (Cambridge) 2016-09, Vol.7 (1), p.647-6412
Main Authors: Li, Guo-Xing, Morales-Rivera, Christian A, Wang, Yaxin, Gao, Fang, He, Gang, Liu, Peng, Chen, Gong
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Summary: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. A photoredox-mediated Minisci C-H alkylation of N -heteroarenes with easily accessible primary and secondary alkyl boronic acids has been developed.
ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc02653b