Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: A versatile trigger for assembling oxygen heterocycles

Journal of the American Chemical Society

Volumn 125, Issue 30, 2003, Pages 9028-9029

  Barluenga, José ^a   Vázquez Villa, Henar ^a   Ballesteros, Alfredo ^a   González, José M ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKYNE; BORIC ACID; CARBON; CARBONYL DERIVATIVE; FLUORINE; HETEROCYCLIC COMPOUND; IODINE; OXYGEN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SYNTHESIS;

EID: 0042367613     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0355372     Document Type: Article

References (45)

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6. For representative examples, see for instance: (a) González, A. G.; Martín, J. D.; Pérez, C.; Ramírez, M. A. Tetrahedron Lett. 1976, 137. (b) Hoye, T. R.; Kurth, M. J. J. Org. Chem. 1978, 43, 3693. (c) Fenical, W. Science 1982, 215, 923. (d) Yamaguchi, Y.; Uyehara, T.; Kato, T. Tetrahedron Lett. 1985, 26, 343. (e) Martín, J. D.; Pérez, C.; Ravelo, J. L. J. Am. Chem. Soc. 1986, 108, 7801. (f) Barluenga, J.; González, J. M.; Campos, P. C.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1546. (g) Kitagawa, O.; Taguchi, T. Synlett 1999, 1191.
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9. For representative examples, see for instance: (a) González, A. G.; Martín, J. D.; Pérez, C.; Ramírez, M. A. Tetrahedron Lett. 1976, 137. (b) Hoye, T. R.; Kurth, M. J. J. Org. Chem. 1978, 43, 3693. (c) Fenical, W. Science 1982, 215, 923. (d) Yamaguchi, Y.; Uyehara, T.; Kato, T. Tetrahedron Lett. 1985, 26, 343. (e) Martín, J. D.; Pérez, C.; Ravelo, J. L. J. Am. Chem. Soc. 1986, 108, 7801. (f) Barluenga, J.; González, J. M.; Campos, P. C.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1546. (g) Kitagawa, O.; Taguchi, T. Synlett 1999, 1191.
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29. The structures depicted for compounds 2 and 6 were based on their spectroscopic and analytical data and were further supported by 2D-NMR studies on 2e, 6a, and 6i and X-ray analysis of 6e (to be published elsewhere).
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37. Vinyl halides having an electron donor group at the β-position are elusive compounds in Sonogashira cross-coupling: (a) Rankin, T.; Tykwinski, R. R. Org. Lett. 2003, 5, 213. We adapted conditions outlined in: (b) Kundu, N. G.; Khan, M. W. Tetrahedron 2000, 56, 4777.
38. Vinyl halides having an electron donor group at the β-position are elusive compounds in Sonogashira cross-coupling: (a) Rankin, T.; Tykwinski, R. R. Org. Lett. 2003, 5, 213. We adapted conditions outlined in: (b) Kundu, N. G.; Khan, M. W. Tetrahedron 2000, 56, 4777.
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40. (b) Barluenga, J.; Llorente, I.; Alvarez-García, L. J.; González, J. M.; Campos, P. J.; Díaz, M. R.; García-Granda, S. J. Am. Chem. Soc. 1997, 119, 6933.
41. For related nitrogen-containing intermediates and its evolution, see, for instance: Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437 and references therein.
42. We reported the fluorinating nature of this condition: (a) Barluenga, J.; Campos, P. J.; González, J. M.; Suárez; J. L.; Asensio, G. J. Org. Chem. 1991, 56, 2234. Besides a metal-free activation of the substrate by the iodonium system fluoride might provide additional activation for the case of silylated nucleophiles: (b) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
43. We reported the fluorinating nature of this condition: (a) Barluenga, J.; Campos, P. J.; González, J. M.; Suárez; J. L.; Asensio, G. J. Org. Chem. 1991, 56, 2234. Besides a metal-free activation of the substrate by the iodonium system fluoride might provide additional activation for the case of silylated nucleophiles: (b) Gauthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363.
44. At present, other alternative pathways cannot be ruled out (we thank one of the referees for valuable comments).
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