A "green" variation of the Hirao reaction: the P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates and secondary phosphine oxides with bromoarenes using a P-ligand-free Pd(OAc) sub(2) catalyst under microwave and solvent-free conditions

The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates, diphenylphosphine oxide and dialkylphosphine oxides with bromoarenes may be performed in the presence of a P-ligand-free Pd(OAc) sub(2) catalyst and triethylamine under microwave-assisted (MW) and, in almost all cases, solvent-free...

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Bibliographic Details
Published in:RSC advances 2014-05, Vol.4 (43), p.22808-22816
Main Authors: Keglevich, Gyorgy, Jablonkai, Erzsebet, Balazs, Laszlo B
Format: Article
Language:English
Subjects:
Alkylation
Catalysts
Inorganic salts
Joining
Microwaves
Oxides
Solvents
Triethylamine
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Summary:The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates, diphenylphosphine oxide and dialkylphosphine oxides with bromoarenes may be performed in the presence of a P-ligand-free Pd(OAc) sub(2) catalyst and triethylamine under microwave-assisted (MW) and, in almost all cases, solvent-free conditions to afford diethyl arylphosphonates, alkyl diphenylphosphinates, aryldiphenylphosphine oxides and dialkylphenylphosphine oxides, respectively. This is the "greenest" accomplishment of the well-known Hirao reaction that has now been found to have general application for a broad spectrum of >P(O)H species with different reactivity and a great variety of substituted bromobenzenes. The alkyl phenyl-H-phosphinates were prepared by the MW-promoted alkylation of phenyl-H-phosphinic acid in the absence of any solvent.
ISSN:2046-2069
DOI:10.1039/c4ra03292f