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DOI: 10.1055/s-2005-863726
Indium Tribromide: A Water-Tolerant Green Lewis Acid
Publication History
Publication Date:
22 February 2005 (online)
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Introduction
Recently, indium tribromide has received increasing attention as a novel type of water-tolerant green Lewis acid catalyst for organic synthesis with highly chemo-, regio- and stereoselective results. [1] Compared to conventional Lewis acids, it has advantages of water stability, recyclability, operational simplicity, strong tolerance to oxygen- and nitrogen-containing reaction substrates and functional groups, and it can often be used in just catalytic amounts. This catalyst promotes various transformations including alknylation of aldehydes and N,O-acetals, [2] Michael addition, [3] synthesis of 1,3-dioxane derivatives, [4] conversion of oxiranes to thiiranes, [5] sulfonation of indoles, [6] alkynylation of acid chorides [7] and synthesis of 2-halo-1,3-dienes. [8]
Indium tribromide is conveniently prepared by heating metallic indium in a current of nitrogen and bromine, [9] and is now also commercially available.
- For recent reviews, see:
-
1a
Fringueli F.Piermatti O.Pizzo F.Vaccaro L. Curr. Org. Chem. 2003, 7: 1661 -
1b
Fan X.-S.Hu X.-Y.Zhang Y.-M. Chin. J. Org. Chem. 2004, 24: 455 - 2
Sakai N.Hirasawa M.Konakahara T. Tetrahedron Lett. 2003, 44: 4177 - 3
Agnusdei M.Bandini M.Melloni A.Umani-Ronchi A. J. Org. Chem. 2003, 68: 7126 - 4
Yadav JS.Reddy BVS.Gakul B. Green Chem. 2003, 5: 264 - 5
Yadav JS.Reddy BVS.Baishya G. Synlett 2003, 396 - 6
Yadav JS.Reddy BVS.Krishna AD.Swamy T. Tetrahedron Lett. 2003, 44: 6055 - 7
Yadav JS.Reddy BVS.Reddy MS.Parimala G. Synthesis 2003, 2390 - 8
Cho YS.Jun BY.Pae AN.Cha JH.Koh HY.Chang MH.Han S.-Y. Synthesis 2004, 2620 - 9
Baxter GP.Alter CM. J. Am. Chem. Soc. 1933, 55: 1943 - 10
Yadav JS.Rao KV.Raj KS.Prasad AR.Kunwar SK.Kunwar AC.Jayaprakash PJ.Jagannath B. Angew. Chem. Int. Ed. 2003, 42: 5198 - 11
Shibata I.Kato H.Ishida T.Yasuda M.Baba A. Angew. Chem. Int. Ed. 2004, 43: 711 - 12
Sakai N.Annaka K.Konakahara T. Org. Lett. 2004, 6: 1527 - 13
Yadav JS.Reddy BVS.Swamy T. Synthesis 2004, 106 - 14
Peppe C.Lang ES.de Andrade FM.de Castro LB. Synlett 2004, 1723 - 15
Kim SH.Shin C.Pae AN.Koh HY.Chang MH.Chung BY.Cho YS. Synthesis 2004, 1581 - 16
Rodríguez RJ.Navarro A. Tetrahedron Lett. 2004, 45: 7495 - 17
Martins MAP.Teixeira MVM.Cunico W.Scapin E.Mayer R.Pereira CMP.Zanatta N.Bonacorso HG.Peppe C.Yuan Y.-F. Tetrahedron Lett. 2004, 45: 8991 -
18a
Yin L.Zhang Z.-H.Wang Y.-M.Pang M.-L. Synlett 2004, 1727 -
18b
Zhang Z.-H.Yin L.Li Y.Wang Y.-M. Tetrahedron Lett. 2005, 46: 889