title: Direct vicinal disubstitution of diaryliodonium salts by pyridine N-oxides and N-amidates by a 1,3-radical rearrangement.
abstract: Paired off: The title reaction leads to a series of o-pyridinium phenols (1) and anilines (2). The experimental and computational studies indicate that the key step involves homolytic cleavage to give a radical pair, which undergoes solvent-cage recombination to give the product.
authors.affiliation: Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Peng
authors.forename: Chao
authors.initials: C
authors.lastname: Chen
authors.forename: Yong
authors.initials: Y
authors.lastname: Wang
authors.forename: Zhenbang
authors.initials: Z
authors.lastname: Lou
authors.forename: Ming
authors.initials: M
authors.lastname: Li
authors.forename: Chanjuan
authors.initials: C
authors.lastname: Xi
authors.forename: Hui
authors.initials: H
authors.lastname: Chen
mesh_terms: D000577:Amides / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry; D018360:Crystallography, X-Ray; D005609:Free Radicals / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D007700:Kinetics; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D012492:Salts / Q000737:chemistry
chemical_list: D000577:Amides; D000814:Aniline Compounds; D005609:Free Radicals; D010636:Phenols; D011725:Pyridines; D012492:Salts; C013229:pyridine N-oxide; D007455:Iodine; C023650:aniline
keywords: arenes; iodonium; radicals; rearrangement; synthetic methods