Iron-Catalyzed ortho-Selective C–H
Borylation of 2‑Phenylpyridines and Their Analogs
Posted on 2017-06-26 - 22:45
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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Yoshigoe, Yusuke; Kuninobu, Yoichiro (2017). Iron-Catalyzed ortho-Selective C–H
Borylation of 2‑Phenylpyridines and Their Analogs. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01423
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AUTHORS (2)
YY
Yusuke Yoshigoe
YK
Yoichiro Kuninobu
KEYWORDS
Phenylpyridineborylated productspresencegram-scalebicyclointramolecularacidpalladium-catalyzed reactionanalogproducts exhibitSelectiveheteroaromatic compoundsBBN9-iron saltBorylationelectroninteractionIron-Catalyzed orthogroup toleranceLewisFeBr 32- phenylpyridinessolutionyieldborylationdimerbondfluoresceAnalogs Treatment