Journal
TETRAHEDRON
Volume 129, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.133144
Keywords
SIBX; Regiospeci fic oxidation; PAH-Metabolite; Hydroxy-PAH; Ortho-quinone
Categories
Funding
- University of Stavanger
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This study demonstrates the conversion of polycyclic aromatic phenols into their corresponding ortho-quinones using stabilized iodoxybenzoic acid. The results show that SIBX is a safer and commercially available alternative to IBX, with similar selectivity and better yields in the oxidative dearomatization reaction.
Polycyclic aromatic phenols (PAPs or hydroxy-PAHs) are conveniently converted into their corresponding ortho-quinones using commercially available stabilized iodoxybenzoic acid (SIBX). SIBX provides a safer and commercially available alternative to IBX and displays the same selectivity with comparable or better yields in the oxidative dearomatization of phenols to ortho-quinone, including examples where forma-tion of para-quinones is feasible. This ortho-selectivity from all positions of a hydroxy-group allowed for simple synthesis of the prerequisite hydroxy-PAHs by either photochemical cyclization of stilbenes or Pt -catalyzed cycloisomerization. The later synthesis involved a four-step sequence where suitably substituted biphenyls were prepared by Suzuki-Miyaura cross-coupling, followed by the Corey-Fuchs protocol and cycloisomerization by a catalytic amount of PtCl2. 2-and 4-methylphenanthene were also prepared for the first time using this method.(c) 2022 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
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