3 years ago

Formaldehyde-Extruding Homolytic Aromatic Substitution via CO Transposition: Selective ‘Traceless-Linker’ access to Congested Biaryl Bonds

Formaldehyde-Extruding Homolytic Aromatic Substitution via CO Transposition: Selective ‘Traceless-Linker’ access to Congested Biaryl Bonds
Kye-Simeon Masters, Kimhoa Chardon, Gabriel dos Passos Gomes, Stefan Bräse, Pabhon Poonpatana, Igor Alabugin, Thomas Hurrle
A new, selective way to form C−C bonds has been developed. In this report, we disclose the homolytic aromatic substitution via CO 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 CO transposition. Access denied: Denying the reaction to proceed via the ortho-position (via substituents) in acetal-linked substrates, a CO transposition coupled with the elimination of formaldehyde (as a traceless linker) is achieved. This allows for a new selective way to form C−C bonds and a new synthetic approach towards highly substituted 2-phenyl phenols.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700085

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