Cr-waste free catalytic carbonyl addition reactions with polymer-immobilized CrF2

Tetrahedron Letters

Volumn 47, Issue 20, 2006, Pages 3395-3399

  Kurosu, Michio ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; AMMONIUM FLUORIDE; BIPYRIDINE DERIVATIVE; CARBONYL DERIVATIVE; CHROMIUM; CHROMIUM DERIVATIVE; POLYMER; RESIN;

ADDITION REACTION; ALLYLATION; ARTICLE; CATALYSIS; DESILYLATION; IMMOBILIZATION;

EID: 33646022243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.071     Document Type: Article

References (30)

1. Kishi Y. Pure Appl. Chem. 64 (1992) 343
2. Denmark S.E., and Fu J. Chem. Rev. 103 (2003) 2763
3. Ling R., Yoshida M., and Mariano P.S. J. Org. Chem. 61 (1996) 4439-4449
4. Kishi Y. Tetrahedron 58 (2002) 6239 and references cited therein
5. Hiyama T., Kimura K., and Nozaki H. Tetrahedron Lett. 22 (1981) 1037
6. Kurosu M., and Lorca M. Tetrahedron Lett. 43 (2002) 1765
7. Fürstner A., and Shi N. J. Am. Chem. Soc. 118 (1996) 2533
8. Fürstner A., and Shi N. J. Am. Chem. Soc. 118 (1996) 12346
9. Singh J., Bridgewater L.C., and Patierno S.R. Toxicol. Sci. 45 (1998) 72
10. O'Brien T., Xu J., and Patierno S.R. Mol. Cell. Biochem. 222 (2001) 173
11. Blaser H.U., Pugin M., and Studer M. Chiral Catalyst Immobilization and Recycling (2000), Wiley-VCH, Weinheim 1
12. Sellner H., Rheiner P.B., and Seebach D. Helv. Chim. Acta 85 (2002) 352
13. Chen C., Tgami K., and Kishi Y. J. Org. Chem. 60 (1995) 5386
14. Sugimoto K., Aoyagi S., and Kibayashi C. J. Org. Chem. 62 (1997) 2322
15. Bandini M., Cozzi P.G., and Umani-Ronchi A. Angew. Chem., Int. Ed. 39 (2000) 2325
16. Bandini M., Cozzi P.G., Melchiorre P., Morganti S., and Umani-Ronchi A. Org. Lett. 3 (2001) 1153
17. Inoue M., Suzuki T., and Nakada M. J. Am. Chem. Soc. 125 (2003) 1140
18. Kurosu M., Lin M.-H., and Kishi Y. J. Am. Chem. Soc. 126 (2004) 12248
19. Glerup J., Josephsen J., Michelsen K., Pedersen E., and Schäffer C.E. Acta Chem. Scand. 24 (1970) 247
20. Kurosu, M.; Kishi, Y., unpublished data.
21. 2O (1 mL) were added. After 6 h, the resins were washed with water, THF-water (3/1), THF, and EtOAc, and dried under high vacuum for 12 h.
22. Liu H., and Montaser A. J. Anal. Spectrom. 11 (1996) 307
23. Boonen S., Vanhaecke F., Moens L., and Dams R. Spectrochim. Acta 51 (1996) 271
24. 2-dipyridyl-TentaGel resins (1.17 g). Total Cr incorporated onto the dipyridyl-TentaGel resins was established as ∼0.3 mmol/g by elemental analysis of Br.
25. - is slower than that with 2.
26. 1H NMR analysis.
27. Among a variety of polymer-supported ammonium fluorides synthesized from the chloromethylated polystyrene, 3 exhibited excellent reactivities in the cleavage of TMS ethers of secondary alcohols. TBDPS group was not cleaved with 3.
28. Total Cr contaminated in the isolated products was less than 0.01 ppm.
29. Mandai T., Nokami J., Yano T., Yoshinaga Y., and Otera J. J. Org. Chem. 49 (1984) 172
30. Namba K., Cui S., Wang J., and Kishi Y. Org. Lett. 7 (2005) 5417 and references cited therein