Benzyl (phenyl) γ- and δ-lactones via photoinduced tandem Ar-C, C-O bond formation

Journal of the American Chemical Society

Volumn 128, Issue 33, 2006, Pages 10670-10671

  Protti, Stefano ^a   Fagnoni, Maurizio ^a   Albini, Angelo ^a  

^a Department of Organic Chemistry ^*  (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROPHENOL; ARGON; BENZENE DERIVATIVE; BENZYL DERIVATIVE; CARBON; CATION; DELTA LACTONE DERIVATIVE; ESTER; GAMMA LACTONE DERIVATIVE; LACTONE DERIVATIVE; OXYGEN; PHENYL DELTA LACTONE; PHENYL GAMMA LACTONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; IRRADIATION; PHOTOCHEMISTRY; PHOTOLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33747795962     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0627287     Document Type: Article

References (22)

1. See for example: Brown, H. C.; Kulkarni, S. V.; Racherla U. S. J. Org. Chem. 1994, 59, 365-369 and references therein.
2. (a) Lambert, J. D.; Rice, J. E.; Hong, J.; Hou, Z.; Yang, C. S. Bioorg. Med. Chem. Lett. 2005, 15, 873-876.
3. (b) Asano, M.; Inoue, M.; Katoh, T. Synlett 2005, 2599-2602.
4. Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366-2368.
5. Sato, M.; Kosasayama, A.; Uchimaru, F. Chem. Pharm. Bull. 1981, 29, 2885-2892.
6. (a) Defieber, C.; Paquin, J.-F.; Serna, S.; Carriera, E. M. Org. Lett. 2004, 6, 3873-3876.
7. (b) Oi, S.; Moro, M.; Ho, H.; Honma, Y.; Miyano, S.; Inoue, Y. Tetrahedron 2002, 58, 91-97.
8. Nagumo, S.; Ishii, Y.; Kakimoto, Y.; Kawahara, N. Tetrahedron Lett. 2002, 43, 5333-5337.
9. A related process is the Pd-catalyzed reaction of aryl bromides with γ-hydroxy alkenes, see: Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621.
10. Fagnoni, M.; Albini, A. Acc. Chem. Res. 2005, 38, 713-721.
11. (a) Chlorides 9, 10b, and 13 did not significantly absorb at > 300 nm. Acetone sensitization was effective for 9 and 10b.
12. (b) A convenient medium such as 2,2,2-trifluoroethanol could not be used in this case because it formed the corresponding trifluoroethyl esters and precluded the formation of the lactones.
13. 2, and the residue was purified by column chromatography.
14. The same reaction carried out in acetonitrile gave 5-(4-(dimethylamino)- benzyl)-dihydro-furan-2-one in about the same yield (70%, see ref 12).
15. Mella, M.; Coppo, P.; Guizzardi, B.; Fagnoni, M.; Freccero, M.; Albini, A. J. Org. Chem. 2001, 66, 6344-6352.
16. Dichiarante, V.; Fagnoni, M.; Mella, M.; Albini, A. Chem.-Eur. J. 2006, 12, 3905-3915.
17. (a) The formation of an oxonium ion has been invoked in related cases.
18. See: (b) Nagumo, S.; Ono, M.; Kakimoto, Y.-L.; Furukawa, T.; Hisano, T.; Mizukami, M.; Kawahara, N. Akita, H. J. Org. Chem. 2002, 67, 6618-6622.
19. (c) Manner, J. A.; Cook, J. A., Jr.; Ramsey, B. G. J. Org. Chem. 1974, 39, 1199-1203.
20. The orthogonal staggered and planar perpendicular open-chain forms of these cations are known to equilibrate with negligible activation energy, see: Hehre, W. J. J. Am. Chem. Soc. 1972, 94, 5919-5920.
21. Kirmse, W. Top. Curr. Chem. 1979, 80, 125-311.
22. Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 7788-7789.