title: Formaldehyde-Extruding Homolytic Aromatic Substitution via C→O Transposition: Selective 'Traceless-Linker' access to Congested Biaryl Bonds.
abstract: 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.
authors.affiliation: Discipline of Nanotechnology and Molecular Sciences, Chemistry, Physics and Mechanical Engineering School, Queensland University of Technology (QUT), GPO Box 2434, Brisbane, Queensland, 4001, Australia.
authors.forename: Pabhon
authors.initials: P
authors.lastname: Poonpatana
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, 32306-4390, USA.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Dos Passos Gomes
authors.affiliation: Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Hurrle
authors.affiliation: Discipline of Nanotechnology and Molecular Sciences, Chemistry, Physics and Mechanical Engineering School, Queensland University of Technology (QUT), GPO Box 2434, Brisbane, Queensland, 4001, Australia.
authors.forename: Kimhoa
authors.initials: K
authors.lastname: Chardon
authors.affiliation: Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.|Institute of Toxicology & Genetics (ITG), Karlsruhe Institute of Technology (KIT), Kaiserstrasse 12, 76131, Karlsruhe, Germany.
authors.forename: Stefan
authors.identifier: http://orcid.org/0000-0003-4845-3191
authors.initials: S
authors.lastname: Bräse
authors.affiliation: Discipline of Nanotechnology and Molecular Sciences, Chemistry, Physics and Mechanical Engineering School, Queensland University of Technology (QUT), GPO Box 2434, Brisbane, Queensland, 4001, Australia.
authors.forename: Kye-Simeon
authors.initials: KS
authors.lastname: Masters
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, 32306-4390, USA.
authors.forename: Igor
authors.initials: I
authors.lastname: Alabugin
keywords: C−C coupling; density functional calculations; radicals; reaction mechanisms; spiro compounds