87688-90-2Relevant articles and documents
Development of the radical C–O coupling reaction of phenols toward the synthesis of natural products comprising a diaryl ether skeleton
Tanaka, Kumpei,Gotoh, Hiroaki
, p. 3875 - 3885 (2019/06/18)
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.
Biomimetic Synthesis of Illicium Oligomeric Neolignans
Sy, Lai-King,Brown, Geoffrey D.
, p. 476 - 477 (2007/10/03)
Six products have been isolated from the oxidative coupling of 4-allylphenol in the presence of FeIII; the distribution of products suggests that oligomeric neolignans associated with the family Illicium may also be non-enzymic products of oxidative coupling.
