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Palladium‐Catalyzed Intramolecular ipso ‐Friedel–Crafts Allylic Alkylation of Phenols via Arylative Activation of Allenes
Author(s) -
Nemoto Tetsuhiro,
Nozaki Tomoyuki,
Yoshida Mariko,
Hamada Yasumasa
Publication year - 2013
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.201300326
Subject(s) - chemistry , intramolecular force , palladium , allene , catalysis , alkylation , friedel–crafts reaction , tsuji–trost reaction , cascade , allylic rearrangement , organic chemistry , phenols , combinatorial chemistry , chromatography
A novel and efficient synthetic method for functionalized spiro[4.5]cyclohexadienones was developed based on the palladium‐catalyzed sequential process: Heck insertion to an allene–intramolecular ipso ‐Friedel–Crafts allylic alkylation cascade. Using 5 mol% of palladium catalyst, a wide variety of spirocycles was obtained in good to excellent yields. The developed cascade process was also applicable to the synthesis of tetrahydronaphthalene derivatives.