ol7b01423_si_001.pdf (8.17 MB)
Iron-Catalyzed ortho-Selective C–H Borylation of 2‑Phenylpyridines and Their Analogs
journal contribution
posted on 2017-06-26, 22:45 authored by Yusuke Yoshigoe, Yoichiro KuninobuTreatment 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.
History
Usage metrics
Categories
Keywords
Phenylpyridineborylated productspresencegram-scalebicyclointramolecularacidpalladium-catalyzed reactionanalogproducts exhibitSelectiveheteroaromatic compoundsBBN9-iron saltBorylationelectroninteractionIron-Catalyzed orthogroup toleranceLewisFeBr 32- phenylpyridinessolutionyieldborylationdimerbondfluoresceAnalogs Treatment
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC