Oxidative, Iodoarene‐Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons. Issue 64 (26th October 2018)

• Record Type: Journal Article
• Authors: Zhao, Zhensheng; Britt, Liam H.; Murphy, Graham K.
• Is Part Of: Chemistry. Volume 24:Issue 64(2018)
• Page Start: 17002
• Page End: 17005
• Publication Date: 2018-10-26
• Subjects: arenes -- hypervalent iodine -- organocatalysis -- polycyclic aromatic hydrocarbons -- vinylenephenonium ion -- vinyliodonium ion; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201804786
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Reacting a mixture of p ‐iodotoluene, m ‐CPBA, and BF3 ⋅OEt2 with ortho ‐vinylbiphenyls results in a metal‐free, oxidative alkene arylation reaction. Various polycyclic aromatic hydrocarbon scaffolds are accessible by this reaction, which appears to proceed via the intermediacy of a vinylenephenonium ion intermediate.