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DOI: 10.1055/s-0030-1258124
Vanadium Oxytrihalide (VOX3)
Publication History
Publication Date:
30 June 2010 (online)
Introduction
Applications of VOX3 (X = F or Cl) in organic synthesis have gained significant importance in recent years. VOX3 are well-known as strong oxidizing agents promoting both intra- and intermolecular oxidative biaryl coupling. This property has been used for synthesis of natural products, [¹,²] phenanthridine, [³] phenanthrene [4] and phenanthrene-9,10-dione [5] derivatives. It were also used for the synthesis of discotic liquid crystalline triphenylene [6] and heteroanalogues. [7] VOX3 also acted as regio- and stereoselective dimerization agents of stilbene derivatives, [8] and as hydroxylation [9] and aromatization [¹0] agents. Other applications of VOX3 are the synthesis of near-infrared absorbent organic semiconductor vanadyl phthalocyanine for organic electronic applications [¹¹,¹²] and the use as catalysts in asymmetric synthesis. [¹³]
-
1a
Su C.-R.Damu AG.Chiang P.-C.Bastow KF.Morris-Natschke SL.Lee K.-H.Wu T.-S. Bioorg. Med. Chem. 2008, 16: 6233 -
1b
Wang K.Wang Q.Huang R. J. Org. Chem. 2007, 72: 8416 -
1c
Evans DA.Wood MR.Trotter BW.Richardson TI.Barrow JC.Katz JL. Angew. Chem. Int. Ed. 1998, 37: 2700 -
1d Evans D. A., Dinsmore
C. J., Watson P. S., Wood M. R., Richardson T. I., Trotter B. W.,
Katz J. L.; Angew. Chem. Int. Ed.; 1998, 37: 2704
-
1e
Evans DA.Dinsmore CJ.Ratz AM.Evrard DA.Barrow JC. J. Am. Chem. Soc. 1997, 119: 3417 - 2
Pettit GR.Meng Y.Gearing RP.Herald DL.Pettit RK.Doubek DL.Chapuis J.-C.Tackett LP. J. Nat. Prod. 2004, 67: 214 - 3
Liepa AJ.Nearn RN.Wright DMJ. Aust. J. Chem. 2004, 57: 473 - 4
Jin Z.Wang Q.Huang R. Synth. Commun. 2004, 34: 119 -
5a
Mohr B.Enkelmann V.Wegner G. J. Org. Chem. 1994, 59: 635 -
5b
Foster EJ.Babuin J.Nguyen N.Williams VE. Chem. Commun. 2004, 2052 -
5c
Lavigueur C.Foster EJ.Williams VE. J. Am. Chem. Soc. 2008, 130: 11791 -
5d
Foster EJ.Jones RB.Lavigueur C.Williams VE. J. Am. Chem. Soc. 2006, 128: 8569 - 6
Weck M.Mohr B.Maughon BR.Grubbs RH. Macromolecules 1997, 30: 6430 -
7a
Babuin J.Foster J.Williams VE. Tetrahedron Lett. 2003, 44: 7003 -
7b
Ichihara M.Suzuki H.Mohr B.Ohta K. Liq. Cryst. 2007, 34: 401 - 8
Velu SS.Buniyamin I.Ching LK.Feroz F.Noorbatcha I.Gee LC.Awang K.Wahab IA.Weber J.-FF. Chem. Eur. J. 2008, 14: 11376 - 9
Hartenstein J.Satzinger G. Angew. Chem. Int. Ed. 1977, 16: 730 -
10a
Filipan-Litvic M.Litvic M.Vinkovic V. Tetrahedron 2008, 64: 10912 -
10b
Gradillas A.del Campo C.Sinisterra JV.Llama EF. J. Chem. Soc., Perkin Trans. 1 1995, 2611 - 11
Villemin D.Hammadi M.Hachemi M.Bar N. Molecules 2001, 6: 831 - 12
Dong S.Tian H.Song D.Yang Z.Yan D.Geng Y.Wang F. Chem. Commun. 2009, 3086 -
13a
Belokon YN.Clegg W.Harrington RW.Maleev VI.North M.Pujol MO.Usanov DL.Young C. Chem. Eur. J. 2009, 15: 2148 -
13b
Belokon YN.Hunt J.North M. Tetrahedron: Asymmetry 2008, 19: 2804 -
13c
Khan N.-uH.Agrawal S.Kureshy RI.Abdi SHR.Prathap KJ.Jasra RV. Eur. J. Org. Chem. 2008, 4511 -
13d
Takizawa S.Katayama T.Somei H.Asano Y.Yoshida T.Kameyama C.Rajesh D.Onitsuka K.Suzuki T.Mikami M.Yamatakay H.Jayaprakash D.Sasai H. Tetrahedron 2008, 64: 3361 -
13e
Belokon YN.Hunt J.North M. Synlett 2008, 2150 -
13f
Belokon YN.Maleev VI.North M.Usanov DL. Chem. Commun. 2006, 4614