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Published on: May 21, 2019
Iron-Catalyzed ortho-Selective C-H Borylation of 2-Phenylpyridines and Their Analogs
Yusuke Yoshigoe1,2, Yoichiro Kuninobu1,2
1Institute for Materials Chemistry and Engineering, Kyushu University , 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan.
Abstract:
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.
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