McMurry coupling of aryl aldehydes and imino pinacol coupling mediated by Ti(O-i-Pr)4/Me3SiCl/Mg reagent

Tetrahedron Letters

Volumn 51, Issue 2, 2010, Pages 387-390

  Okamoto, Sentaro ^a   He, Jing Qian ^a   Ohno, Chihaya ^a   Oh iwa, Yuhji ^a   Kawaguchi, Yuhki ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CHLORIDE; IMINO ACID; MAGNESIUM; SILICON; TITANIUM;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; CHEMICAL MODIFICATION; CROSS COUPLING REACTION; MCMURRY COUPLING REACTION; PINACOL REARRANGEMENT; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 71049137301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.027     Document Type: Article

References (24)

1. McMurry J.E., and Fleming M.P. J. Am. Chem. Soc. 96 (1974) 4708
2. Mukaiyama T., Sato T., and Hanna J. Chem. Lett. (1973) 1041
3. McMurry J.E. Chem. Rev. 89 (1989) 1513
4. Lenoir D. Synthesis (1989) 883
5. Kahn B.E., and Rieke R.D. Chem. Rev. 88 (1988) 733
6. Fürstner A., and Bogdanovic B. Angew. Chem., Int. Ed. 35 (1996) 2442
7. Ephritikhine M. Chem. Commun. (1998) 2549
8. Sato F., Urabe H., and Okamoto S. Chem. Rev. 100 (2000) 2835
9. Kulinkovich O.G., and de Meijere A. Chem. Rev. 100 (2000) 2789
10. Eisch J.J. J. Organomet. Chem. 617-618 (2001) 148
11. Sato F., and Okamoto S. Adv. Synth. Catal. 343 (2001) 759
12. Sato F., and Urabe H. In: Marek I. (Ed). Titanium and Zirconium in Organic Synthesis (2002), Wiley-VCH, Weinheim, Germany 319-354
13. Rele A.M., Nayak S.K., and Chattopadhyay S. Tetrahedron 64 (2008) 7225 and references cited therein
14. Ohkubo M., Mochizuki S., Sano T., Kawaguchi Y., and Okamoto S. Org. Lett. 9 (2007) 773
15. For pinacol coupling, see:. Lipski T.A., Hilfiker M.A., and Nelson S.G. J. Org. Chem. 62 (1997) 4566 and references cited therein
16. Review for imino pinacol coupling:. Lucet D., Le Gall T., and Mioskowski C. Angew. Chem., Int. Ed. 37 (1998) 2580
17. Periasamy M., Srinivas G., Karunakar G.V., and Bharathi P. Tetrahedron Lett. 40 (1999) 7577
18. Cooke A.W., and Wagener K.B. Macromolecules 24 (1991) 1404
19. Demir A.S., and Reis O. Tetrahedron 60 (2004) 3803
20. Anuragudom P., Newaz S.S., Phanichphant S., and Lee T.R. Macromolecules 39 (2006) 3494
21. Jiu T., Li Y., Liu X., Liu H., Li C., Ye J., and Zhu D. J. Polym. Sci., Part A: Polym. Chem. 45 (2007) 911
22. Liu Q., Liu W., Yao B., Tian H., Xie Z., Geng Y., and Wang F. Macromolecules 40 (2007) 1851
23. Faugeroux V., Génisson Y., Salma Y., Constant P., and Baltas M. Bioorg. Med. Chem. 15 (2007) 5866 and references cited therein
24. 3SiCl (0.254 mL, 2.00 mmol) at room temperature. The mixture was stirred for 20-24 h at this temperature and then quenched by the addition of aqueous 1 M NaOH (∼0.5 mL). After addition of NaF (∼1 g) and Celite (∼1 g), the resulting mixture was stirred for 1 h and then filtrated through a pad of Celite. The filtrate was concentrated to dryness and the residue was purified by column chromatography on silica gel (hexane/AcOEt) to give 1,2-diarylethylene-1,2-diamine 6.