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Revisiting the Hirao Cross-coupling: Improved Synthesis of Aryl and Heteroaryl Phosphonates.

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.

SUBMITTER: Belabassi Y 

PROVIDER: S-EPMC2587344 | biostudies-literature | 2008 Jan

REPOSITORIES: biostudies-literature

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Revisiting the Hirao Cross-coupling: Improved Synthesis of Aryl and Heteroaryl Phosphonates.

Belabassi Yamina Y   Alzghari Saeed S   Montchamp Jean-Luc JL  

Journal of organometallic chemistry 20080101 19

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. ...[more]

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