Categories: C-P Bond Formation >
Synthesis of phosphonates
| Synthesis of | |||
| α-Hydroxy phosphonates |  |
α-Amino phosphonates |  |
Name Reactions
Recent Literature
A two step procedure involving a transesterification between a diol and
diethyl phosphite followed by a palladium-catalyzed coupling of the so-obtained
cyclic phosphite with vinyl bromide gave vinyl phosphonates in good yields.
M. Maffei, G. Buono, Tetrahedron, 2003, 59, 8821-8825.
A convenient and efficient copper-catalyzed approach for P-arylation of
organophosphorus compounds containing P-H uses the commercially available and
inexpensive proline and pipecolinic acid as ligands. The method can provide an
entry to arylphosphonates, arylphosphinates and arylphosphine oxides.
C. Huang, X. Tang, H. Fu, Y. Jiang, Y. Zhao, J. Org. Chem., 2006, 71, 4951-4955.
When treated with a radical initiator selenophosphates,
selenophosphorodithioates, selenophosphorothioates and
selenophosphorotrithioates
undergo homolytic cleavage of the P-Se bond to generate radicals. Addition onto electron-rich and electron-poor alkenes
in the presence of a hydrogen donor delivers the expected adducts in good yields.
C. Lopin, G. Gouhier, A. Gautier, S. R. Piettre, J. Org. Chem.,
2003, 68, 9916-9923.
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