Photomediated synthesis of β-alkylketones from cycloalkanes

Tetrahedron

Volumn 62, Issue 23, 2006, Pages 5527-5535

  Dondi, Daniele ^a   Cardarelli, Anna Maria ^a   Fagnoni, Maurizio ^a   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

Alkanes; Alkylation; C H activation; Enones; Photochemistry; Radicals and radical reactions

Indexed keywords

BENZOPHENONE; CYCLOADAMANTANE; CYCLOALKANE DERIVATIVE; CYCLODODECANE; CYCLOHEPTANE DERIVATIVE; CYCLOHEXANE; CYCLOPENTANE; HYDROGEN; INORGANIC COMPOUND; KETONE DERIVATIVE; ORGANIC COMPOUND; RADICAL; REAGENT; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM DECATUNGSTATE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYST; MEDIATOR; PERFUSION; PHOTOCATALYSIS; PHOTOSYNTHESIS; PRECURSOR; PRIORITY JOURNAL;

EID: 33748081796     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.028     Document Type: Article

References (60)

1. Liu J.-Y., Jang Y.-J., Lin W.-W., Liu J.-T., and Yao C.-F. J. Org. Chem. 68 (2003) 4030-4038 and reference cited therein
2. Jang D.O., and Cho D.H. Synlett (2002) 631-634
3. Arndsten B.A., Bergman R.G., Mobley T.A., and Peterson T.H. Acc. Chem. Res. 28 (1995) 154-162
4. Pamplin C.B., and Legzdins P. Acc. Chem. Res. 36 (2003) 223-233
5. Jia C., Kitamura T., and Fujiwara Y. Acc. Chem. Res. 34 (2001) 633-639
6. Shilov A.E., and Shul'pin G.B. Chem. Rev. 97 (1997) 2879-2932
7. Komiya S., and Hirano M. In: Murahashi S.-I. (Ed). Ruthenium in Organic Synthesis (2004), Wiley-VCH, Weinheim 345-355
8. Larsch M., and Tilset M. Chem. Rev. 105 (2005) 2471-2526
9. Tabushi I., and Fukunishi K. J. Org. Chem. 39 (1974) 3748-3750
10. Metzger J., Hartmanns J., and Koll P. Tetrahedron Lett. 22 (1981) 1891-1894
11. Fokin A.A., and Schreiner P.R. Adv. Synth. Catal. 345 (2003) 1035-1052
12. Interesting results have been obtained by using phase-transfer chemistry; See:. Schreiner P.R., Lauenstein O., Butova E.D., Gunchenko P.A., Kolomitsin I.V., Wittkopp A., Feder G., and Fokin A.A. Chem. Eur. J. 7 (2001) 4996-5003
13. Fokin A.A., and Schreiner P.R. Chem. Rev. 102 (2002) 1551-1594
14. Albini A., and Fagnoni M. Chim. Oggi. 22 (2005) 36-38
15. Cardarelli A.M., Fagnoni M., Mella M., and Albini A. J. Org. Chem. 66 (2001) 7320-7327
16. Campari G., Mella M., Fagnoni M., and Albini A. Tetrahedron: Asymmetry 11 (2000) 1891-1906
17. Gonzalez-Cameno A.M., Mella M., Fagnoni M., and Albini A. J. Org. Chem. 65 (2000) 297-303
18. Doohan R.A., and Geraghty N.W.A. Green Chem. 7 (2005) 91-96
19. Manfrotto C., Mella M., Freccero M., Fagnoni M., and Albini A. J. Org. Chem. 64 (1999) 5024-5028
20. Fraser-Reid B., Anderson R.C., Hisks D.R., and Walker D.L. Can. J. Chem. 55 (1977) 3986-3995
21. Kisch H. Adv. Photochem. 26 (2001) 93-143
22. Dondi D., Fagnoni M., Molinari A., Maldotti A., and Albini A. Chem. Eur. J. 10 (2004) 142-148
23. Ruhlen J.L., and Leermakers P.A. J. Am. Chem. Soc. 89 (1967) 4944-4948
24. Lam E.Y.Y., Valentine D., and Hammond G.S. J. Am. Chem. Soc. 89 (1967) 3482-3487
25. Wolff S., Schreiber W.L., Smith A.B., and Agosta W. J. Am. Chem. Soc. 94 (1972) 7797-7806
26. The term 'chemical sensitization' has also been used for this process, the most common case being 'Type I' photooxygenation.
27. Bell J.A., and Linschitz H. J. Am. Chem. Soc. 85 (1963) 528-533
28. Schuster D.I., and Brizzolara D.F. J. Am. Chem. Soc. 92 (1970) 4357-4365
29. Arnaut L.G., Caldwell R.A., Elbert J.E., and Melton L.A. Rev. Sci. Instrum. 63 (1992) 5381-5389
30. Schuster D.J., Heibel G.E., Caldwell R.A., and Tang W. Photochem. Photobiol. 52 (1990) 645-648
31. The triplet energy of 3-buten-2-one 2j has shown to be difficult to determine but probably ranges from 250 to 294 kJ/mol; see. Garcia-Exposito E., Bearpark M.J., Ortuno R.M., Branchadell V., Robb M.A., and Wilsey S. J. Org. Chem. 66 (2001) 8811-8814
32. Bonneau R. J. Am. Chem. Soc. 102 (1980) 3816-3822
33. The same difference had been previously observed in the photomediated radical addition of 1,3-dioxolan-2-yl radicals onto enones. See Ref. 21.
34. Mosca R., Fagnoni M., Mella M., and Albini A. Tetrahedron 57 (2001) 10319-10328
35. See also Dondi, D.; Fagnoni, M; Albini, A. Chem.-Eur. J., doi:10.1002/chem.200501216.
36. Tanielian C., Seghrouchni R., and Schweitzer C. J. Phys. Chem. A 107 (2003) 1102-1111
37. Giering L., Berger M., and Steel C. J. Am. Chem. Soc. 96 (1974) 953-958
38. Johnston L.J., Lougnot D.J., Wintgens V., and Scaiano J.C. J. Am. Chem. Soc. 110 (1988) 518-524
39. 6-. See:. Tanielian C. Coord. Chem. Rev. 178-180 (1998) 1165-1181
40. Actually, as it has been shown in the literature, a mixture of 1- and 2-electron reduced decatungstate is formed. See. Yamase T., Takabayashi N., and Kaji M. J. Chem. Soc., Dalton Trans. (1984) 793-799
41. Tanielian C., Seghrouchni R., and Schweitzer C. J. Phys. Chem. A 107 (2003) 1102-1111
42. Shield S.R., and Harris J.M. Anal. Chem. 70 (1998) 2576-2583
43. -1; see:. Naguib Y.M.A., Steel C., and Cohen S.G. J. Phys. Chem. 91 (1987) 3033-3036
44. -1. Tanielian C., Duffy K., and Jones A. J. Phys. Chem. B 101 (1997) 4276-4282
45. This is the middle value between the rate constant for the addition of the methyl and the t-Bu radicals onto acrolein; see:. Fischer H., and Radom L. Angew. Chem. 113 (2001) 1380-1414
46. Angew. Chem., Int. Ed. Engl. 40 (2001) 1340-1371
47. Beckwith A.L.J., and Poole J.S. J. Am. Chem. Soc. 124 (2002) 9489-9497
48. Recupero F., Bravo A., Bjørsvik H.-R., Fontana F., Minisci F., and Piredda M. J. Chem. Soc., Perkin Trans. 2 (1997) 2399-2406
49. Demeter A., and Bérces T. J. Phys. Chem. 95 (1991) 1228-1232
50. Dondi D., Caprioli I., Fagnoni M., Mella M., and Albini A. Tetrahedron 59 (2003) 947-957
51. The polytungstate was effective for 50 cycles under the present conditions. Doubling the amount of polytungstate in the synthesis of 3bk led to only a small increase of the yield (44% with respect to 35%) whereas the yields dropped to 20.5% when using 0.2 M (in the place of 0.1 M) olefin.
52. Yamase T., and Usami T. J. Chem. Soc., Dalton Trans. (1988) 183-190
53. Ono N., Kamimura A., Miyake H., Hamamoto I., and Kaji A. J. Org. Chem. 50 (1985) 3692-3698
54. Jones P., Reddy C.K., and Knochel P. Tetrahedron 54 (1998) 1471-1490
55. Collins P.W., Gasiecki A.F., Perkins W.E., Gullikson G.W., Jones P.H., and Bauer R.F. J. Med. Chem. 32 (1989) 1001-1006
56. Wipf P., Xu W., and Smitrovich J. Tetrahedron 50 (1994) 1935-1954
57. Baguley P.A., and Walton J.C. J. Chem. Soc., Perkin Trans. 1 (1998) 2073-2082
58. Liu J., Jang Y., Lin W., Liu J., and Yao C. J. Org. Chem. 68 (2003) 4030-4038
59. Ohno M., Ishizaki K., and Eguchi S. J. Org. Chem. 53 (1988) 1285-1288
60. Petrier C., De Souza Barbosa J., Dupuy C., and Luche J.L. J. Org. Chem. 50 (1985) 5761-5765