Titanium Tetrachloride (TiCl₄)

Introduction

Titanium tetrachloride (TiCl₄) is one of the most important and typical Lewis acids. Its strong affinity towards oxygenated organic compounds and powerful dehydrating action are manifested in various functional group transformations. [1] TiCl₄ has emerged as an efficient Lewis acid catalyst in organic chemistry. A number of reviews are available on the preparation and reactions of lower valent Ti. [2]

Recently TiCl₄ was efficiently used as a catalyst in various important reactions, which include the enantioselective synthesis of γ-amino acids and γ-lactones, [3] alkylation of carbonyl compounds, [4] pinacol coupling, [5] pyrollidine synthesis, [6] Claisen rearrangement, [7] oxepene synthesis [8] and asymmetric aldol reaction, [9] etc.

References

• 1a For more details see: Paquette LA. Encyclopedia of Reagents for Organic Synthesis   Vol. 5:  John Wiley & Sons; New York: 1995.  p.4913; and references cited there in 
• (b) Muraiyama T. Angew. Chem. Int. Ed.  1997,  16:  817 
• 2a Betschart C. Seebach D. Chimia  1989,  43:  39 
• 2b Pons J.-M. Santelli M. Tetrahedron  1988,  44:  4295 
• 2c Reetz MT. Organotitanium Reagents in Organic Synthesis   Springer; Berlin: 1986.  p.223 
• 3 Brenner M. Seebach D. Helv. Chim. Acta  1999,  82:  2365 
• 4 Lahi G. Petrovski Z. Golonic D. Motavic R. Sai RN. Tetrahedron Lett.  2000,  41:  763 
• 5 Li T. Cui W. Zhang J. Wang Z. Chem. Commun.  2000,  7:  139 
• 6 Miura K. Honda T. Nakagawa T. Takaheshi Y. Hosomi A. Org. Lett.  2000,  2:  385 
• 7 Yoon TP. Dong VM. MacMillan DWC. J. Am. Chem. Soc.  1999,  121:  9726 
• 8 Fujiwara K. Amoto A. Tokiwano T. Murai A. Tetrahedron  2000,  56:  1065 
• 9 Crimmins MT. Choudhery K. Org. Lett.  2000,  2:  775 
• 10 Periasamy M. Srinivas G. Karunakar GV. Bharathi P. Tetrahedron Lett.  1999,  40:  7577 
• 11 Liguori L. Bjorsvik HR. Fontane F. Bosco D. Galimberti L. Minisci F. J. Org. Chem.  1999,  64:  8812 
• 12 Kakaoka T. Kinoshita H. Kinoshita T. Iswamura T. Watanabe S. Angew. Chem. Int. Ed.  2000,  39:  2358 
• 13 Ding Y.-X. Hu JJ. Chem. Soc., Perkin. Trans 1  2000,  10:  1651 
• 14 Knowles HS. Parsons AF. Pettifer RM. Rickling S. Tetrahedron  2000,  56:  979 
• 15 Tsuritani T. Shinokubo H. Oshima K. Tetrahedron Lett.  1999,  40:  8112