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DOI: 10.1055/s-0031-1291016
Titanium(III) Trichloride
Publikationsverlauf
Publikationsdatum:
26. April 2012 (online)
Introduction
Titanium(III) chloride is red-violet crystalline solid soluble in water and alcohol. It has been extensively used as a mild and useful reagent with diverse applications in organic synthesis, such as reduction of aromatic aldehydes, glycosyl halides, vicinal dihalides, sulfoxides,[ 1 ] oximes,[2] [3] [4] [5] hydroxamic acids,[ 6 ] nitro group,[ 7 ] and dehalogenation of α-halo ketones.[ 8 ] In addition, the aqueous TiCl3/NH3 system has been used to promote the reduction of aromatic aldehydes, ketenes, and diketones to give alcohols.[9] [10] Reductive cyclizations of oxoamides to produce indoles can also be effectively promoted by TiCl3.[ 11 ] Apart from these applications, TiCl3 is also known as a Lewis acid to catalyze the SnCl2-mediated Barbier reactions between aldehydes and allyl halides in aqueous media.[ 12 ]
TiCl3 is commercially available and can be synthesized by dissolving titanium in aqueous hydrochloric acid.
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References
- 1 Jana S, Guin C, Roy SC. Tetrahedron Lett. 2004; 45: 6575
- 2 Maslov MA, Morozova NG, Solomatina TV, Sergeeva OA, Cheshkov DA, Serebrennikova GA. Mendeleev Commun. 2011; 21: 137
- 3 Bolger JK, Tian W, Wolter WR, Cho W, Suckow MA, Miller MJ. Org. Biomol. Chem. 2011; 9: 2999
- 4 Tabolin AA, Khomutova YA, Nelyubina YV, Ioffe SL, Tartakovsky VA. Synthesis 2011; 2415
- 5 Wilkinson SM, Watson MA, Willis AC, McLeod MD. J. Org. Chem. 2011; 76: 1992
- 6 Mattingly PG, Miller MJ. J. Org. Chem. 1980; 45: 410
- 7 Crozet MD, George P, Crozet MP, Vanelle P. Molecules 2005; 10: 1318
- 8 Ho T.-L, Wong CM. Synth. Commun. 1973; 3: 237
- 9 Clerici A, Pastori N, Porta O. Eur. J. Org. Chem. 2002; 3326
- 10 Clerici A, Pastori N, Porta O. Eur. J. Org. Chem. 2001; 2235
- 11 Fürstner A, Ernst A, Krause H, Ptock A. Tetrahedron 1996; 52: 7329
- 12 Tan X.-H, Hou Y.-Q, Huang C, Liu L, Guo Q.-X. Tetrahedron 2004; 60: 6129
- 13 Zhang Y, Tang Q, Luo MM. Org. Biomol. Chem. 2011; 9: 4977
- 14 Lin Z.-P, Li J.-T, Li T.-S. Lett. Org. Chem. 2006; 3: 278
- 15 Bian YJ, Hu CX. Chin. J. Org. Chem. 2011; 31: 1695
- 16 Clerici A, Pastori N, Porta O. Eur. J. Org. Chem. 2002; 3326
- 17 Lee CL, Huang CH, Wang HC, Chuang DW, Wu MJ, Wang SY, Hwang TL, Wu CC, Chen YL, Chang FR, Wu YC. Org. Biomol. Chem. 2011; 9: 70
- 18 Pratsch G, Anger GA, Ritter K, Heinrich MR. Chem.–Eur. J. 2011; 17: 4104
- 19 Drug E, Gozin M. J. Am. Chem. Soc. 2007; 129: 13784
- 20 Cannella R, Clerici A, Pastori N, Regolini E, Porta O. Org. Lett. 2005; 7: 645