Organic Letters
Organic Letters
5 years ago

Iron-Catalyzed ortho-Selective C–H Borylation of 2-Phenylpyridines and Their Analogs

Iron-Catalyzed ortho-Selective C–H Borylation of 2-Phenylpyridines and Their Analogs
Yoichiro Kuninobu, Yusuke Yoshigoe
Treatment of 2-phenylpyridines (or their analogs) with a 9-bicycloboranonane dimer (9-BBN dimer) in the presence of a catalytic amount of a commercially available iron salt, FeBr3, gave ortho-borylated products in moderate to excellent yields with good functional group tolerance. The reaction proceeded in good yield, even in gram-scale, and also occurred at the C–H bond of heteroaromatic compounds. The cost of the C–H borylation is dramatically lower than that of a previously reported similar palladium-catalyzed reaction. The products exhibit an intramolecular B–N Lewis acid–base interaction and fluoresce in both solution and solid states due to their electron push–pull structures.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01423

DOI: 10.1021/acs.orglett.7b01423

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