Oxidative, Iodoarene‐Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons | Zendy

Zhao Zhensheng | Zendy; Britt Liam H. | Zendy; Murphy Graham K. | Zendy

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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

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.

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