Journal
TETRAHEDRON
Volume 75, Issue 29, Pages 3875-3885Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.05.035
Keywords
Diaryl ether skeleton; Phenol; Radical; Coupling reaction
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Compounds comprising a diaryl ether skeleton exist among natural phenols. The diaryl ether skeleton is thought to be biosynthesized through the coupling of two or more phenols. It is an important structural feature in medicines and agrochemicals, and it is imperative to develop methods for constructing such skeletons in organic synthesis. However, by the synthesis method through the coupling of phenols, coupling occurs preferentially at the ortho-substituted carbon atom of phenols. In this study, various radical-generating reagents and conditions were investigated with the aim of developing a short-step construction method of the diaryl ether skeleton by the radical homo-coupling of two phenol molecules. In addition, cross-coupling reactions between radicals of 2,4,6-tri-tert-butylphenol and p-substituted phenol were conducted to synthesize eight C (ortho)-O coupling products. Based on the results, a computational chemical approach was employed to verify the cause of C (ortho)-O bond formation. (C) 2019 Elsevier Ltd. All rights reserved.
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