Title:Polydopamine-Modified Magnetic Nanoparticles (Fe3O4@PDA) for the
Copper-Catalyzed Ipso-Hydroxylation of Arylboronic Acids and
Subsequent O-Benzylation in Aqueous Media
Volume: 21
Issue: 10
Author(s): Kwang-Beom Lee, Ueon Sang Shin*Seung-Hoi Kim*
Affiliation:
- Department of Nanobiomedical
Science, BK21 FOUR NBM Global Research Center for Regenerative Medicine, Dankook University, Cheonan, 31116,
Republic of Korea
- Institute of Tissue Regeneration Engineering (ITREN), Dankook University, Cheonan, 31116,
Republic of Korea
- Department of Chemistry, Dankook University, Cheonan, 31116, Republic of Korea
Keywords:
Magnetite, polydopamine, copper-catalyzed, aerobic ipso-hydroxylation, O-benzylation, arylboronic acids.
Abstract: A novel advancement has emerged in the realm of catalysis with the development of an
innovative method for the Ipso-hydroxylation of arylboronic acids. This approach harnessed the
power of bio-compatible polydopamine-coated magnetite support (Fe3O4@PDA) in conjunction with
a copper salt, forming a heterogeneous catalytic environment. The resulting catalytic system facilitated
oxidative hydroxylation under mild aerobic conditions at room temperature in aqueous conditions.
This environmentally friendly process allowed for the seamless conversion of diverse arylboronic
acids featuring varying electron-withdrawing or electron-donating groups into the corresponding
phenols, achieving remarkably high yields. Notably, the versatility of the catalytic system
extended to a one-pot tandem O-benzylation of the resultant phenolic intermediates. The additional
dimension of the process underscores its efficiency, offering a streamlined route to synthesizing benzyl
phenyl ethers with a commendable level of success. The significance of the present catalytic
methodology lies not only in its efficacy but also in its eco-friendly attributes, showcasing the potential
for sustainable and efficient transformations in organic synthesis.
