Categories: C-P Bond Formation >
Synthesis of phosphonates
| Synthesis of | |||
| α-Hydroxy phosphonates |  |
α-Amino phosphonates |  |
Name Reactions
Recent Literature
Using a prevalent palladium catalyst, Pd(PPh3)4, a
quantitative cross-coupling of various H-phosphonate diesters with aryl and
vinyl halides was achieved in less than 10 min under microwave irradiation. The
reactions occurred with retention of configuration at the phosphorus center and
in the vinyl moiety.
M. Kalek, A. Ziadi, J. Stawinski, Org. Lett.,
2008,
10, 4637-4640.
A mild and efficient copper-catalyzed addition of H-phosphonate dialkyl esters
to boronic acids gives aryl phosphonates using Cu2O/1,10-phenanthroline
as catalytic system.
R. Zhuang, J. Xu, Z. Cai, G. Tang, M. Fang, Y. Zhao, Org. Lett., 2011,
13, 2110-2113.
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.
An efficient method allows the synthesis of benzylphosphonate diesters via a
palladium(0)-catalyzed cross-coupling reaction between benzyl halides and
H-phosphonate diesters, using Pd(OAc)2 as a palladium source and
Xantphos as a supporting ligand.
G. Lavéna, J. Stawinski, Synlett, 2009,
225-228.
A Lewis acid-mediated Michaelis-Arbuzov reaction of arylmethyl halides and
alcohols with triethyl phosphite at room temperature enables a facile
preparation of arylmethyl and heteroarylmethyl phosphonate esters in good yields.
G. G. Rajeshwaran, M. Nandakumar, R. Sureshbabu, A. K. Mohanakrishnan, Org. Lett., 2011,
13, 1270-1273.
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.
A low-ligated palladium/triphenylphosphane catalytic system in the presence of a
catalytic amount of trifluoroacetic acid allows a hydrophosphorylation of
terminal and internal alkynes with high isolated yields and excellent regio- and
stereoselectivity. The catalytic system permits the formation of diverse
alkenylphosphonates utilizing various available H-phosphonates and alkynes.
V. P. Ananikov, L. L. Khemchyan, I. P. Beletskaya, Synlett, 2009,
2375-2381.
Copper-catalyzed aerobic oxidative coupling of terminal alkynes with
H-phosphonates affords alkynylphosphonates in high yields.
Y. Gao, G. Wang, L. Chen, P. Xu, Y. Zhao, Y. Zhou, L.-B. Han, J. Am. Chem. Soc., 2009,
131, 7956-7957.
A new, efficient method based on a palladium(0)-catalyzed reaction of
propargylic derivatives with various phosphorus nucleophiles produces
allenylphosphonates and their analogues with defined stereochemistry in the
allenic and the phosphonate moiety.
M. Kalek, T. Johansson, M. Jezowska, J. Stawinski, Org. Lett., 2010,
12, 4702-4704.
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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