Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine. Issue 10 (18th July 2016)

• Record Type: Journal Article
• Authors: Li, Guo-Xing; Morales-Rivera, Christian A.; Wang, Yaxin; Gao, Fang; He, Gang; Liu, Peng; Chen, Gong
• Is Part Of: Chemical science. Volume 7:Issue 10(2016:Oct.)
• Page Start: 6407
• Page End: 6412
• Publication Date: 2016-07-18
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6sc02653b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A photoredox-mediated Minisci C–H alkylation of N -heteroarenes with easily accessible primary and secondary alkyl boronic acids has been developed. 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.