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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Polydopamine-Modified Magnetic Nanoparticles (Fe3O4@PDA) for the Copper-Catalyzed Ipso-Hydroxylation of Arylboronic Acids and Subsequent O-Benzylation in Aqueous Media

Author(s): Kwang-Beom Lee, Ueon Sang Shin* and Seung-Hoi Kim*

Volume 21, Issue 10, 2024

Published on: 12 March, 2024

Page: [889 - 897] Pages: 9

DOI: 10.2174/0115701786294756240305063556

Price: $65

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.

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