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Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates
Authors:Yamina Belabassi
Institution:Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, TX 76129, USA
Abstract:The palladium-catalyzed cross-coupling of dialkylphosphite with aromatic electrophiles (Hirao coupling) was re-investigated. Some limitations in terms of palladium loadings and substrate reactivity are alleviated with the use of Pd(OAc)2 complexed to 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand. Various aryl and heteroaryl halides are employed to deliver both known and novel substituted phosphonates. The first examples of aryl chloride couplings are also reported.
Keywords:Cross-coupling  Phosphorus  Palladium  Heterocycles  Aryl halides
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