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Cu/Pd‐Catalyzed C‐2–H Arylation of Quinazolin‐4(3 H )‐ones with (Hetero)aryl Halides
Author(s) -
Godeau Julien,
Harari Marine,
Laclef Sylvain,
Deau Emmanuel,
Fruit Corinne,
Besson Thierry
Publication year - 2015
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.201501129
Subject(s) - aryl , iodobenzene , halide , chemistry , catalysis , palladium , combinatorial chemistry , ligand (biochemistry) , medicinal chemistry , organic chemistry , biochemistry , alkyl , receptor
The regiospecific C‐2–H arylation of N‐3‐substituted quinazolin‐4(3 H )‐ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand‐dependent palladium/copper bicatalytic system was developed and allowed direct cross‐coupling with a variety of (hetero)aryl halides. This useful and scalable procedure promotes the construction of C(sp 2 )–C(sp 2 ) bonds from arenes or (hetero)arenes and aryl or (hetero)aryl bromides and chlorides in a time‐efficient strategy. The extension of the reaction to various N‐3‐substituted quinazolin‐4(3 H )‐ones with iodobenzene as well as the scope and limitations of the method were also investigated.