Silver(I)-catalyzed cascade: Direct access to furans from alkynyloxiranes

Journal of Organic Chemistry

Volumn 74, Issue 11, 2009, Pages 4360-4363

  Blanc, Aurélien ^a   Tenbrink, Katharina ^a   Weibel, Jean Marc ^a   Pale, Patrick ^a  

^a Institut de Chimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE MECHANISM; CATALYZED REACTIONS; CHEMICAL EQUATIONS; DIRECT ACCESS; FUNCTIONALIZED; OXIRANES; PTOLUENESULFONIC ACID;

CHEMICAL REACTIONS; METHANOL; SILVER; SULFUR COMPOUNDS;

SILVER COMPOUNDS;

ETHYLENE OXIDE DERIVATIVE; FURAN DERIVATIVE; METHANOL; SILVER; TOLUENESULFONIC ACID DERIVATIVE;

AROMATIZATION; ARTICLE; CATALYSIS; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION OPTIMIZATION;

ALKYNES; CATALYSIS; ETHYLENE OXIDE; FURANS; SILVER;

EID: 66249147550     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900483m     Document Type: Article

References (47)

1. (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795-819.
2. (b) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955-2020.
3. (c) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 2001, 2491-2515.
4. (a) Eicher, T.; Hauptmann S. The Chemistry of Heterocycles, 2nd ed.; Wiley-VCH: Weinheim, 2003.
5. (b) Bird, C. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven E. F. V., Eds.; Elsevier Science Ltd.; Oxford, 1996; Vol.2.
6. Miller, D. J. Chem. Soc. C 1969, 12-15.
7. (a) Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem. 1987, 334, 225-242.
8. (b) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816-5819.
9. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 1995, 34, 1581-1583.
10. (d) Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089-13102.
11. (e) Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288.
12. (f) Ma, S. M.; Zhang, J. L.; Lu, L. H. Chem. - Eur. J. 2003, 9, 2447-2456.
13. Yoshida, M.; Al-Amin, M.; Matsuda, K. S. Tetrahedron Lett. 2008, 49, 5021-5023.
14. (a) Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022-15023.
15. (b) Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024-15025.
16. (c) Fürstner, A.; Heilmann, E. K.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 4760-4763.
17. Hashmi, A. S. K.; Pradipta, S. Adv. Synth. Catal. 2004, 346, 432-438.
18. (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J. H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288.
19. (b) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164-11165.
20. (c) Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679-7685.
21. (d) Shu, X.-Z.; Liu, X.-Y.; Xiao, H.-Q.; Ji, K.-G.; Guo, L.-N.; Qi, C.-Z.; Liang, Y.-M. Adv. Synth. Catal. 2007, 349, 2493-2498.
22. (e) Ji, K.-G.; Shen, Y.-M.; Shu, X.-Z.; Xiao, H.-Q.; Bian, Y.-J.; Liang, Y.-M. Adv. Synth. Catal. 2008, 350, 1275-1280.
23. (f) Dai, L.-Z.; Shi, M. Tetrahedron Lett. 2008, 49, 6437-6439.
24. For recent reviews on silver chemistry, see: (a) Weibel, J.-M.; Blanc, A. P.; Pale, Chem. Rev. 2008, 108, 3149-3173.
25. (b) Alvarez-Corral, M.; Munoz-Dorado, M.; Rodriguez-Garcia, I. Chem. Rev. 2008, 108, 3174-3198.
26. (c) Yamamoto, Y. Chem. Rev. 2008, 108, 3199-3222.
27. (d) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395-3442.
28. (e) Halbes-Letinois, U.; Weibel, J.-M.; Pale, P. Chem. Soc. Rev. 2007, 36, 759-769.
29. Marshall, J. A.; Robinson, E. D. J. Org. Chem. 1990, 55, 3450-3451.
30. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966-5968.
31. Hayes, S. J.; Knight, D. W.; Menzies, M. D.; O'Halloran, M.; Tan, W.-F. Tetrahedron Lett. 2007, 48, 7709-7712.
32. Arimitsu, S.; Hammond, G. B. J. Org. Chem. 2007, 72, 8559-8567.
33. (a) Chuche, J.; Pale, P. Tetrahedron Lett. 1987, 28, 6447-6448.
34. (b) Dalla, V.; Pale, P. Tetrahedron Lett. 1996, 37, 2781-2784.
35. (c) Chuche, J.; Pale, P. Eur. J. Org. Chem. 2000, 1019-1025.
36. (a) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron Lett. 1989, 30, 2387-2390.
37. (b) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677-1686.
38. (a) Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191-3194.
39. (b) Shu, X.-Z.; Liu, X.-Y.; Ji, K.-G.; Xiao, H.-Q.; Liang, Y.-M. Chem. - Eur. J. 2008, 14, 5282-5289.
40. (c) Hashmi, A. S. K.; Bührle, M.; Salathé, R.; Bats, J. W. Adv. Synth. Catal. 2008, 350, 2059-2064.
41. (d) Lin, G.-Y.; Li, C.-W.; Hung, S.-H.; Liu, R.-S. Org. Lett. 2008, 10, 5059-5062.
42. (e) Dai, L.-Z.; Shi, M. Chem. - Eur. J. 2008, 14, 7011-7018.
43. For a review of alkynyloxirane preparations, see: Chemla, F.; Ferreira, F. Curr. Org. Chem. 2002, 6, 539-570.
44. Compound 1a was obtained following Carlson's procedure: Carlson, R. G.; Cox, W. W. J. Org. Chem. 1977, 42, 2382-2386.
45. Traces of water or alcohols contained in the solvent or the reagents were probably responsible for catalysis of this reaction (see Scheme 4), and carefully dried solvent and reagents have to be used to miminize it.
46. Nucleophiles based on other heteroatoms probably poisoned the catalyst, while carbon nucleophiles are currently explored.
47. Cordonnier, M.-C.; Blanc, A.; Pale, P. Org. Lett. 2008, 10, 1569-1572.