Abstract
A general and greener protocol for the synthesis of aryl phosphonates by the cross-coupling of aryl halides and diethyl phosphite using tetrakis(triphenylphosphine)palladiume/triethylamine/polyethylene glycol 600 [Pd(PPh3)4/Et3N/PEG 600] as an efficient catalytic system has been developed. This procedure also avoids hazardous solvents and is therefore an eco-friendly alternative to the existing methods.
References
1.
Galezowska J.
, and
Gumienna-Kontecka E.
, Coord. Chem. Rev. , 2012 , 256 , 105 .
2.
Surry D.S.
, and
Buchwald S.L.
, Chem. Sci. , 2011 , 2 , 27 .
3.
Wei Y.
, and
Shi M.
, Acc. Chem. Res. , 2010 , 43 , 1005 .
4.
Guenin E.
, and
Meziane D.
, Curr. Org. Chem. , 2011 , 15 , 3465 .
5.
Van der Jeught S.
, and
Stevens C.V.
, Chem. Rev. , 2009 , 109 , 2672 .
6.
Mehtaa V.P.
, and
Van der Eycken E.V.
, Chem. Soc. Rev. , 2011 , 40 , 4925 .
7.
Tappe F.M.J.
,
Trepohl V.T.
, and
Oestreich M.
, Synthesis , 2010 , 3037 .
8.
Hirao T.
,
Masunaga T.
,
Ohshiro Y.
, and
Agawa T.
, Synthesis , 1981 , 56 .
9.
Kalek M.
,
Jezowska M.
, and
Stawinski J.
, Adv. Synth. Catal. , 2009 , 351 , 3207 .
10.
Kalek M.
,
Ziadi A.
, and
Stawinski J.
, Org. Lett. , 2008 , 10 , 4637 .
11.
Belabassi Y.
,
Alzghari S.
, and
Montchamp J.L.
, J. Organomet. Chem. , 2008 , 693 , 3171 .
12.
Kohler M.C.
,
Sokol J.G.
, and
Stockland R.A.
, Tetrahedron Lett. , 2009 , 50 , 457 .
13.
Petrakis K.S.
, and
Nagabhushan T.L.
, J. Am. Chem. Soc. , 1987 , 109 , 2831 .
14.
Shen C.R.
,
Yang G.Q.
, and
Zhang W.B.
, Org. Biomol. Chem. , 2012 , 10 , 3500 .
15.
Andaloussi M.
,
Lindh J.
,
Savmarker J.
,
Sjoberg P.J.R.
, and
Larhed M.
, Chem. Eur. J. , 2009 , 15 , 13069 .
16.
Zhuang R.Q.
,
Xu J.A.
,
Cai Z.S.
,
Tang G.
,
Fang M.J.
, and
Zhao Y.F.
, Org. Lett. , 2011 , 13 , 2110 .
17.
Luo Y.
, and
Wu J.
, Organometallics , 2009 , 28 , 6823 .
18.
Hou C.D.
,
Ren Y.L.
,
Lang R.
,
Hu X.X.
,
Xia C.G.
, and
Li F.W.
, Chem. Commun. , 2012 , 48 , 5181 .
19.
Zhang Z.H.
, Monatsh. Chem. , 2005 , 136 , 1191 .
20.
Singh U.P.
, Synlett , 2012 , 2721 .
21.
Zhang X.N.
,
Li Y.X.
, and
Zhang Z.H.
, Tetrahedron , 2011 , 67 , 7426 .
22.
Karnakar K.
,
Murthy S.N.
,
Ramesh K.
,
Satish G.
,
Nanubolu J.B.
, and
Nageswar Y.V.D.
, Tetrahedron Lett. , 2012 , 53 , 2897 .
23.
Yao L.F.
,
Zhou Q.
,
Han W.
, and
Wei S.H.
, Eur. J. Org. Chem. , 2012 , 6856 .
24.
Mallepalli R.
,
Yeramanchi L.
,
Bantu R.
, and
Nagarapu L.
, Synlett , 2011 , 2730 .
25.
Nagarapu L.
,
Mallepalli R.
,
Yeramanchi L.
, and
Bantu R.
, Tetrahedron Lett. , 2011 , 52 , 3401 .
26.
Guo R.Y.
,
Wang P.
,
Wang G.D.
,
Mo L.P.
, and
Zhang Z.H.
, Tetrahedron , 2013 , 69 , 2056 .
27.
Zhang Z.H.
,
Zhang X.N.
,
Mo L.P.
,
Li Y.X.
, and
Ma F.P.
, Green Chem. , 2012 , 14 , 1502 .
28.
Liu Y.-H.
,
Deng J.
,
Gao J.-W.
, and
Zhang Z.-H.
, Adv. Synth. Catal. , 2012 , 354 , 441 .
29.
Deng J.
,
Mo L.P.
,
Zhao F.Y.
,
Zhang Z.H.
, and
Liu S.X.
, ACS Comb. Sci. , 2012 , 14 , 335 .
30.
Wang H.J.
,
Mo L.P.
, and
Zhang Z.H.
, ACS Comb. Sci. , 2011 , 13 , 181 .
31.
Deng J.
,
Mo L.P.
,
Zhao F.Y.
,
Hou L.L.
,
Yang L.
, and
Zhang Z.H.
, Green Chem. , 2011 , 13 , 2576 .
32.
Zhang Z.H.
,
Lu H.Y.
,
Yang S.H.
, and
Gao J.W.
, J. Comb. Chem. , 2010 , 12 , 643 .
33.
Villemin D.
,
Elbilali A.
,
Simeon F.
,
Jaffres P.A.
,
Maheut G.
,
Mosaddak M.
, and
Hakiki A.
, J. Chem. Res. (S) , 2003 , 436 –437 .
34.
Freedman L.D.
, and
Jaffe H.H.
, J. Am. Chem. Soc. , 1955 , 77 , 920 –921 .
35.
Garner G.V.
,
Mobbs D.B.
,
Suschitzky H.
, and
Millership J.S.
, J. Chem. Soc. (C) , 1971 , 3693 .
36.
Allen D.W.
,
Hutley B.G.
, and
Mellor M.T.J.
, J. Chem. Soc. Perkin 2 , 1977 , 789 .