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Formaldehyde‐Extruding Homolytic Aromatic Substitution via C→O Transposition: Selective ‘Traceless‐Linker’ access to Congested Biaryl Bonds
Author(s) -
Poonpatana Pabhon,
dos Passos Gomes Gabriel,
Hurrle Thomas,
Chardon Kimhoa,
Bräse Stefan,
Masters KyeSimeon,
Alabugin Igor
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700085
Subject(s) - homolysis , transposition (logic) , linker , chemistry , steric effects , substitution (logic) , formaldehyde , combinatorial chemistry , stereochemistry , radical , organic chemistry , computer science , artificial intelligence , programming language , operating system
A new, selective way to form C−C bonds has been developed. In this report, we disclose the homolytic aromatic substitution 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.