Direct lactone formation by using hypervalent iodine(III) reagents with KBr via selective C-H abstraction protocol

Organic Letters

Volumn 9, Issue 16, 2007, Pages 3129-3132

  Dohi, Toshifumi ^a   Takenaga, Naoko ^a   Goto, Akihiro ^a   Maruyama, Akinobu ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; BROMIDE; CARBOXYLIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IODINE; LACTONE; PHTHALIMIDE DERIVATIVE; POTASSIUM BROMIDE; POTASSIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BENZOIC ACIDS; BROMIDES; CARBOXYLIC ACIDS; INDICATORS AND REAGENTS; IODINE; LACTONES; MOLECULAR STRUCTURE; PHTHALIMIDES; POTASSIUM COMPOUNDS;

EID: 34547950171     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071315n     Document Type: Article

References (48)

1. (a) Collins, I. J. Chem. Soc., Perkin Trans. 1 1998, 1869.
2. (b) Donnelly, D. M. X.; Meegan, M. J. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon: New York, 1984; Vol. 4, p 657.
3. (c) Devon, T. K.; Scott, A. I. In Handbook of Naturally Occurring Compounds; Academic Press: New York, 1975; Vol. 1, 249.
4. (a) Carroll, A. R.; Taylor, W. C Aust. J. Chem. 1991, 44, 1615.
5. (b) Katzenellenbogen, J. A.; Rai, R.; Dai, W. Bioorg. Med. Chem. Lett. 1992, 2, 1399.
6. (c) Hwang, E.-I.; Yun, B.-S.; Kim, Y.-K.; Kwon, B.-M.; Kim, H.-G.; Lee, H.-B.; Jeong, W.-J.; Kim, S.-U. J. Antibiot. 2000, 53, 903.
7. (d) Husain, A.; Khan, M. S. Y.; Hasan, S. M.; Alam, M. M. Eur. J. Med. Chem. 2005, 40, 1394.
8. (e) Lambert, J. D.; Rice, J. E.; Hong, J.; Hou, Z.; Yang, C. S. Bioorg. Med. Chem. Lett. 2005, 15, 873.
9. (a) Brauman, J. I.; Pandell, A. J. J. Am. Chem. Soc. 1970, 92, 329.
10. (b) Nagarajan, A.; Porchezhiyan, V.; Srinivasaramanujam; Balasubramanian, T. R. Ind. J. Chem. 1985, 24B, 1202.
11. (c) Irie, H.; Maruyama, J.; Shimada, M.; Zhang, Y.; Kouno, I.; Shimamoto, K.; Ohfune, Y. Synlett 1990, 421.
12. γ-Lactone formation from aliphatic carboxylic acids having suitably activated benzyl positions: Jevric, M.; Taylor, D. K.; Greatrex, B. W.; Tiekink, E. R. T. Tetrahedron 2005, 67, 1885.
13. (a) Kochi, J. K. J. Org. Chem. 1965, 30, 3265.
14. (b) Kochi, J. K.; Bacha, J. D. J. Org. Chem. 1968, 33, 2746.
15. (c) Sheldon, R. A.; Kochi, J. K. Org. React. 1972, 19, 279.
16. For recent reviews: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
17. (b) Kita, Y.; Takada, T.; Tohma, H. Pure Appl. Chem. 1996, 68, 627.
18. (c) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, CA, 1997.
19. (d) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409.
20. (e) Ochiai, M. In Chemistry in Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
21. (f) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
22. (g) Hypervalent Iodine Chemistry; Wirth, T., Ed.; Springer-Verlag: Berlin, Germany, 2003.
23. (h) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893.
24. (i) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656.
25. Benzylic azidation of phenyl ethers with phenyliodine bis(trifluoroacetate): Kita, Y.; Tohma, H.; Takada, T.; Mitoh, S.; Fujita, S.; Gyoten, M. Synlett 1994, 427.
26. Generation and detection of active iodine(III)-Br species in water by the combination of PIDA or iodosobenzene with KBr, see: (a) Tohma, H.; Takizawa, S.; Maegawa, T.; Kita, Y. Angew. Chem., Int. Ed. 2000, 39, 1306.
27. (b) Tohma, H.; Maegawa, T.; Takizawa, S.; Kita, Y. Adv. Synth. Catal. 2002, 344, 328.
28. Iodine(III) oxidations in the presence of bromide. LiBr or NaBr: (a) Braddock, D. C; Cansell, G.; Hermitage, S. A. Synlett 2004, 461.
29. (b) Karade, N. N.; Shirodkar, S. G.; Dhoot, B. M.; Waghmare, P. B. J. Chem. Res. 2005, 274. Ammonium bromide:
30. (c) Hashem, M. A.; Jung, A.; Ries, M.; Kirschning, A. Synlett 1998, 195.
31. (d) Brunjes, M.; Sourkouni-Argirusi, G.; Kirschning, A. Adv. Synth. Catal. 2003, 345, 635. TMSBr:
32. (e) Evans, P. A.; Brandt, T. A. J. Org. Chem. 1997, 62, 5321.
33. In Group 1 alkali metal bromide, yield of 2a decreased in order with KBr > NaBr »LiBr. LiBr induced remarkable bromination at both aromatic and benzyl carbons.
34. (a) Hayat, S.; Atta-ur-Rahman; Choudhary, M. I.; Khan, K. M.; Bayer, E. Tetrahedron Lett. 2001, 42, 1647.
35. (b) Kikuchi, D.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6023.
36. 4. After removal of the solvents, the residue was subjected to silica gel column chromatography (eluents: n-hexane/AcOEt) to give the y-phenyl y-butyrolactone 3a (65 mg, 80%) as a white powder. Unreacted 2a (9.8 mg, 12%) was recovered from the combined aqueous phase by extraction of dichloromethane after acidifying the solution.
37. (a) Pohmakotr, M.; Pinsa, A.; Mophuang, T.; Tuchinda, P.; Prabpai, S.; Kongsaeree, P.; Reutrakul, V. J. Org. Chem. 2006, 71, 386.
38. (b) Yamauchi, S.; Hayashi, Y.; Nakashima, Y.; Kirikihira, T.; Yamada, K.; Masuda, T. J. Nat. Prod. 2005, 68, 1459.
39. (c) Brown, R. C. D.; Bataille, C. J. R.; Bruton, G.; Hinks, J. D.; Swain, N. A. J. Org. Chem. 2001, 66, 6719.
40. (d) Yoda, H.; Kimura, K.; Takabe, K. Synlett 2001, 400.
41. (e) Yoshida, S.; Ogiku, T.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1995, 36, 1459.
42. - and TMSBr produce hypobromite or the bromate(I) complex and molecular bromine, respectively. See, refs 9c-e.
43. Isolation of cyclic 1(III)-Br compounds and their use as radical initiators: Amey, R. L.; Martin, J. C. J. Am. Chem. Soc. 1979, 10, 3060.
44. Direct phthalide formation with metal oxidants: (a) Lee, J. M.; Chang, S. Tetrahedron Lett. 2006, 47, 1375 and references cited therein,
45. (b) Creighton, A. M.; Jackman, L. M. J. Chem. Soc. 1960, 3138.
46. (c) Mahmoodi, N. O.; Salehpour, M. J. Heterocycl. Chem. 2003, 40, 875.
47. Phthalide formation with hypervalent iodine(III) reagents under UV irradiation was reported with few example of substrates; however, the procedure was not applicable to aliphatic carboxylic acids because of the rapid decarboxylation: (a) Togo, H.; Muraki, T.; Yokoyama, M. Tetrahedron Lett. 1995, 36, 7089.
48. (b) Muraki, T.; Togo, H.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1999, 1713.