Cu/Pd‐Catalyzed C‐2–H Arylation of ­Quinazolin‐4(3H)‐ones with (Hetero)aryl Halides. Issue 35 (6th November 2015)

• Record Type: Journal Article
• Authors: Godeau, Julien; Harari, Marine; Laclef, Sylvain; Deau, Emmanuel; Fruit, Corinne; Besson, Thierry
• Is Part Of: European journal of organic chemistry. Issue 35(2015)
• Page Start: 7705
• Page End: 7717
• Publication Date: 2015-11-06
• Subjects: Nitrogen heterocycles -- Microwave chemistry -- C–H functionalization -- Cross‐coupling -- Palladium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501129
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 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 is studied.