On the paradox of TiCl4 reducing power: Pinacol coupling and two-carbon homologation of carbonyl compounds

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1825-1827

  Clerici, Angelo ^a   Pastori, Nadia ^a   Porta, Ombretta ^a  

^a Dipto Chim Industriale I   (Italy)

Author keywords

Carbon homologation; DIPEA; Electron transfer; Pinacol coupling; Titanium tetrachloride

Indexed keywords

ALCOHOL; ALDEHYDE; CARBON; CARBONYL DERIVATIVE; CHLORINE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; PINACOL REARRANGEMENT; REDUCTION;

EID: 1242316320     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.025     Document Type: Article

References (20)

1. Evans D.A., Urpi F., Somers T.C., Clark J.S., Bilodeau M.T. J. Am. Chem. Soc. 112:1990;8215-8216.
2. Evans D.A., Clark J.S., Metternich R., Novack V.J., Sheppard G.S. J. Am. Chem. Soc. 112:1990;866-868.
3. Evans D.A., Rieger D.L., Bilodeau M.T., Urpi F. J. Am. Chem. Soc. 113:1991;1047-1049.
4. Figueras S., Martin R., Romea P., Urpi F., Vilarrasa J. Tetrahedron Lett. 38:1997;1637-1640.
5. Crimmins M.T., King B.W., Tabet E. J. Am. Chem. Soc. 119:1997;7883-7884.
6. Adrian J.J.C., Barkin J.L., Fox R.J., Chick J.E., Hunter A.D., Nicklow R.A. J. Org. Chem. 65:2000;6264-6267.
7. For a selected review, see: Arya P., Qin H. Tetrahedron. 56:2000;917. and references cited therein.
8. Crimmins M.T., King B.W., Tabet E.A., Chandhardy K. J. Org. Chem. 66:2001;894-902.
9. Chosh A.K., Kim J.H. Tetrahedron Lett. 43:2002;5621-5624. and references cited therein.
10. Yoshida Y., Hayashi R., Sumihara H., Tanabe Y. Tetrahedron Lett. 38:1997;8727-8730. see note 11.
11. 4 complexation with DIPEA.
12. 1f.
13. Enamines without hydrogen on the nitrogen, as F, are normally stable: March J. Advanced Organic Chemistry. 1985;John Wiley, New York. pp 69-70 and references cited therein.
14. 3): δ 6.70 (1H, dd, J=7.9 , 15.9 Hz); 7.42 (1H, d, J=15.9 Hz); 7.43 (2H, ArH, d, J=8.8 Hz); 7.58 (2H, ArH, d, J=8.8 Hz); 9.71 (1H CHO, d, J=7.9 Hz). MS (CI): m/z 213-211 (M + 1, 100).
15. 2, s) ; 7.24 (2H, ArH, d, J=8.2 Hz); 7.48 (2H, ArH, d, J=8.2 Hz).
16. Clerici A., Clerici L., Porta O. Tetrahedron Lett. 37:1996;3035-3038.
17. 3/NaOH aqueous solution, owing to the increased reducing power of Ti(III) in basic medium. Clerici A., Porta O. J. Org. Chem. 50:1985;76-81.
18. Clerici A., Pastori N., Porta O. Eur J. Org. Chem. 2002;3326-3335.
19. Clerici A., Porta O. J. Org. Chem. 47:1982;2852-2856.
20. Clerici A., Porta O. J. Org. Chem. 50:1985;76-82.