Efficient and selective alkylation of arenes and heteroarenes with benzyl and allyl ethers using a Ir/Sn bimetallic catalyst

Tetrahedron

Volumn 63, Issue 37, 2007, Pages 9146-9152

  Podder, Susmita ^a   Roy, Sujit ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIMETHYLFURAN; 4 BROMOANISOLE; ALLYL COMPOUND; ANISOLE; BENZENE; BENZYL DERIVATIVE; BROMOBENZENE; IRIDIUM; ORTHO XYLENE; PARA XYLENE; POLYCYCLIC AROMATIC HYDROCARBON; THIOPHENE; TIN; TOLUENE; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; ARTICLE; BENZYLATION; CATALYST; DRUG SOLUBILITY; PRIORITY JOURNAL;

EID: 34547431603     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.068     Document Type: Article

References (54)

1. Schmidt F., Stemmler R.T., Rudolph J., and Bolm C. Chem. Soc. Rev. 35 (2006) 454
2. Khan M.S., Al-Mandhary M.R.A., Al-Suti M.K., Ahrens B., Mahon M.F., Male L., Raithby P.R., Boothby C.E., and Kohler A. J. Chem. Soc., Dalton Trans. (2003) 74
3. Jacob J., Oldridge L., Zhang J.Y., Gaal M., List E.J.W., Grimsdale A.C., and Müllen K. Curr. Appl. Phys. 4 (2004) 339
4. Olah G.A. Friedel-Crafts and Related Reactions Vol II (1964), Wiley Interscience, New York, NY Part I
5. Roberts R.M., and Khalaf A.A. Friedel-Crafts Alkylation Chemistry. A Century of Discovery (1984), Marcel Dekker, New York, NY
6. Burwell Jr. R.L. Chem. Rev. 54 (1954) 615
7. For Overview:
8. In: Yamamoto H. (Ed). Lewis Acids in Organic Synthesis Vols. 1 and 2 (2000), Wiley-VCH, Weinheim, Germany
9. Corma A., and Garcia H. Chem. Rev. 103 (2003) 4307
10. Bandini M., Melloni A., and Umani-Ronchi A. Angew. Chem. Int. Ed. 43 (2004) 550
11. Kobayashi S., and Ogawa C. Chem.-Eur. J. 12 (2006) 5954
12. Selected References:
13. Fürstner A., Voigtländer D., Schrader W., Giebel D., and Reetz M.T. Org. Lett. 3 (2001) 417
14. Mertins K., Jovel I., Kischel J., Zapf A., and Beller M. Angew. Chem., Int. Ed. 44 (2005) 238
15. Rueping M., Nachtsheim B.J., and Ieawsuwana W. Adv. Synth. Catal. 348 (2006) 1033
16. Rueping M., Nachtsheim B.J., and Scheidt T. Org. Lett. 8 (2006) 3717
17. Ishii A., Kotera O., Saeki T., and Mikami K. Synlett (1997) 1145
18. Mukaiyama T., Ueki M., Izawa T., and kuwahara M. Chem. Lett. (1972) 443
19. Tsuchimoto T., Tobita K., Hiyama T., and Fukuzawa S. J. Org. Chem. 62 (1997) 6997
20. Shiina I., and Suzuki M. Tetrahedron Lett. 43 (2002) 6391
21. Sinha P., and Roy S. Organometallics 23 (2004) 67
22. Banerjee M., and Roy S. Org. Lett. 6 (2004) 2137
23. Banerjee M., and Roy S. J. Mol. Cat. A: Chem. 246 (2006) 231
24. Choudhury J., Podder S., and Roy S. J. Am. Chem. Soc. 127 (2005) 6162
25. Podder S., Choudhury J., and Roy S. J. Org. Chem. 72 (2007) 3129
26. Clayden J., Greeves N., Warren S., and Wothers P. Organic Chemistry (2001), Oxford University Press, Oxford, UK Chapter 41, pp 1090-1100
27. Walter, R.; Kirchner, S.; Franz, R. U.S. Patent 6,399,804, 2002.
28. Yamashita M. Synthesis (1977) 803
29. Kim S., Chung K.N., and Yang S. J. Org. Chem. 52 (1987) 3917
30. Kayaki Y., Koda T., and Ikariya T. J. Org. Chem. 69 (2004) 2595
31. Nguyen Van T., Debenedetti S., and Kimpe N.D. Tetrahedron Lett. 44 (2003) 4199
32. Wright S.W., Hageman D.L., Wright A.S., and McClure L.D. Tetrahedron Lett. 38 (1997) 7345
33. Lygo B., O'connor N., and Wilson P.R. Tetrahedron 44 (1988) 6881
34. Sereda G.A. Tetrahedron Lett. 45 (2004) 7265
35. Lee M.J., Lee K.Y., Park D.Y., and Kim J.N. Tetrahedron 62 (2006) 3128
36. Kofink C.C. Org. Lett. 8 (2006) 4121
37. Karade N.N. J. Chem. Res., Synop (2003) 652
38. Nakai Y., and Yamada F. Org. Magn. Reson. 11 (1978) 607
39. Sefkow M., and Buchs J. Org. Lett. 5 (2003) 193
40. Nakai Y., Takabayashi T., and Yamada F. Org. Magn. Reson. 13 (1980) 94
41. Climent M.J., Corma A., Garcia H., and Primo J. J. Catal. 130 (1991) 138
42. Mironov G.S., Farberov M.I., Timoshenko G.N., and Kazanskaya V.A. Zh. Org. Khim. 6 (1970) 1453
43. Mahindaratne M.P.D., and Wimalasena K. J. Org. Chem. 63 (1998) 2858
44. John J. Organometallics 24 (2005) 6291
45. Grobelny Z. J. Organomet. Chem. 660 (2002) 6
46. Ng C.T. J. Org. Chem. 53 (1988) 2536
47. Herve A. J. Org. Chem. 70 (2005) 1953
48. Petchmanee T. J. Org. Chem. 71 (2006) 2892
49. Saha M. Bangladesh J. Sci. Ind. Res. 36 (2001) 64
50. Zhang S., Marshall D., and Liebeskind L.S. J. Org. Chem. 64 (1999) 2796
51. Giannangeli M. Tetrahedron 36 (1980) 1381
52. Ichihara J. Chem. Commun. (1997) 1921
53. Sarca V.D. Green Chem. 8 (2006) 615
54. Chahen L. Synlett (2003) 1668