Biphenyl-2-ols undergo regioselectivemono- and diarylation upon a treatment with aryl iodides in the presence of a palladium catalyst in DMF using Cs2CO3 as a base to produce 1,1′ : 2′,1″-terphenyl-2-ol and 2′,6′-diphenylbiphenyl-2-ol and their derivatives. The reaction of 1-naphthol selectively occurs at its 8-position to give 8-aryl-1-naphthols. In the reaction of 2-naphthol with aryl bromides, diarylated
Formaldehyde-Extruding Homolytic Aromatic Substitution via C→O Transposition: Selective ‘Traceless-Linker’ access to Congested Biaryl Bonds
作者:Pabhon Poonpatana、Gabriel dos Passos Gomes、Thomas Hurrle、Kimhoa Chardon、Stefan Bräse、Kye-Simeon Masters、Igor Alabugin
DOI:10.1002/chem.201700085
日期:2017.7.6
A new, selective way to form C−C bonds has been developed. In this report, we disclose the homolytic aromaticsubstitution via C→O transposition coupled with the elimination of formaldehyde (as a traceless linker). Computational analysis indicates the selectivity can be tuned by sterics in the starting materials following an ipso‐attack that leads to the C→O transposition.