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Oxidative, Iodoarene‐Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons
Author(s) -
Zhao Zhensheng,
Britt Liam H.,
Murphy Graham K.
Publication year - 2018
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.201804786
Subject(s) - hypervalent molecule , intramolecular force , alkene , chemistry , catalysis , yield (engineering) , oxidative coupling of methane , reagent , medicinal chemistry , organic chemistry , materials science , metallurgy
Abstract A catalytic, metal‐free and chemoselective oxidative intramolecular coupling of arene and alkene C−H bonds is reported. The active hypervalent iodine (HVI) reagent, generated catalytically in situ from iodotoluene and meta‐ chloroperoxybenzoic acid (m ‐CPBA), reacts with o ‐vinylbiphenyls to generate polyaromatic hydrocarbons in up to 95 % yield. Experimental evidence suggests the reactions proceed though vinyliodonium and, possibly, vinylenephenonium intermediates.