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Copper‐Catalyzed Oxidative Ring Closure of ortho ‐Cyanoanilides with Hypervalent Iodonium Salts: Arylation–Ring Closure Approach to Iminobenzoxazines
Author(s) -
Aradi Klára,
Novák Zoltán
Publication year - 2015
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.201400763
Subject(s) - hypervalent molecule , chemistry , ring (chemistry) , copper , trifluoromethanesulfonate , catalysis , closure (psychology) , medicinal chemistry , aryl , oxidative phosphorylation , combinatorial chemistry , organic chemistry , alkyl , iodine , biochemistry , economics , market economy
A novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho ‐cyanoanilides and diaryliodonium triflates via an oxidative arylation–cyclization path. The reaction is supposed to involve the formation of highly active aryl‐copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2‐dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2–16 h.