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2,3‐Dichloro‐5,6‐dicyano‐ para ‐benzoquinone (DDQ)/Methanesulfonic Acid (MsOH)‐Mediated Intramolecular Arene‐Alkene Oxidative Coupling
Author(s) -
Kim Ko Hoon,
Lim Cheol Hee,
Lim Jin Woo,
Kim Jae Nyoung
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201301169
Subject(s) - chemistry , intramolecular force , alkene , methanesulfonic acid , hydrogen atom abstraction , oxidative coupling of methane , medicinal chemistry , photochemistry , benzoquinone , catalysis , substrate (aquarium) , organic chemistry , radical , oceanography , geology
An efficient intramolecular arene‐alkene oxidative coupling of 1,4‐diaryl‐1,3‐butadienes has been developed involving the use of a 2,3‐dichloro‐5,6‐dicyano‐ para ‐benzoquinone (DDQ)/acid catalyst. The reaction involves the generation of a radical cation by abstraction of an electron from the substrate with DDQ, an intramolecular Friedel–Crafts‐type reaction, and the loss of hydrogen radical.