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Microwave‐Promoted Palladium‐Catalysed Oxyarylation of Dihydronaphthalene and Chromenes by o ‐Iodophenols and Its Acetates
Author(s) -
Leão Raquel A. C.,
Pinho Vagner D.,
Coelho Artur S.,
Buarque Camilla D.,
Moraes Paula F.,
Alonso Diego A.,
Nájera Carmen,
Costa Paulo R. R.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100365
Subject(s) - chemistry , acetone , palladium , yield (engineering) , oxime , medicinal chemistry , solvent , base (topology) , catalysis , organic chemistry , mathematical analysis , materials science , mathematics , metallurgy
The oxyarylation of dihydronaphthalene ( 1a ), two electron‐rich ( 1b , c ) and one electron‐poor ( 2 ) chromenes with different o ‐iodophenols and their acetates 3a – h has been investigated by using either Pd(OAc) 2 (10 mol‐%) as precatalyst and Ag 2 CO 3 as base in acetone as solvent or oxime palladacycle 5 as precatalyst and dicyclohexylamine as base in DMA/H 2 O. The reactions, which were strongly accelerated under microwave heating, afforded the best yields when electron‐rich chromenes reacted with o ‐iodophenols substituted by electron‐withdrawing groups in the presence Pd(OAc) 2 and Ag 2 CO 3 . However, in the case of electron‐poor chromenes the best yield was obtained with the electron‐rich o ‐iodophenol 3g .