Three-component coupling using arynes and isocyanides: straightforward access to benzo-annulated nitrogen or oxygen heterocycles

Tetrahedron

Volumn 63, Issue 22, 2007, Pages 4793-4805

  Yoshida, Hiroto ^a   Fukushima, Hiroyuki ^a   Morishita, Takami ^a   Ohshita, Joji ^a   Kunai, Atsutaka ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Aryne; Isocyanide; Nitrogen heterocycle; Oxygen heterocycle; Three component coupling

Indexed keywords

ALDEHYDE; BENZOFURAN DERIVATIVE; BENZOQUINONE DERIVATIVE; CYANIDE; HETEROCYCLIC COMPOUND; IMINE; ISOINDOLE DERIVATIVE; KETONE DERIVATIVE; NITROGEN; OXYGEN;

ADDITION REACTION; ANNULATION REACTION; ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 34247272920     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.042     Document Type: Article

References (54)

1. For reviews, see:
2. Hoffmann R.W. Dehydrobenzene and Cycloalkynes (1967), Academic, New York, NY
3. Pellissier H., and Santelli M. Tetrahedron 59 (2003) 701-730
4. Rondan N.G., Domelsmith L.N., Houk K.N., Bowne A.T., and Levin R.H. Tetrahedron Lett. 20 (1979) 3237-3240
5. For a review on nucleophilic couplings with arynes, see:. Kessar S.V. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford 483-515
6. For examples, see:
7. Sato Y., Toyooka T., Aoyama T., and Shirai H. J. Org. Chem. 41 (1976) 3559-3564
8. Nakayama J., Takeue S., and Hoshino M. Tetrahedron Lett. 25 (1984) 2679-2682
9. Hayashi S., and Ishikawa N. Bull. Chem. Soc. Jpn. 45 (1972) 642-644
10. N-C σ-bond:
11. Yoshida H., Shirakawa E., Honda Y., and Hiyama T. Angew. Chem., Int. Ed. 41 (2002) 3247-3249 S-Sn σ-bond:
12. Yoshida H., Terayama T., Ohshita J., and Kunai A. Chem. Commun. (2004) 1980-1981 N-Si σ-bond:
13. Yoshida H., Minabe T., Ohshita J., and Kunai A. Chem. Commun. (2005) 3454-3456 C-C σ-bond:
14. Yoshida H., Watanabe M., Ohshita J., and Kunai A. Chem. Commun. (2005) 3292-3294
15. Yoshida H., Watanabe M., Ohshita J., and Kunai A. Tetrahedron Lett. 46 (2005) 6729-6731
16. Tambar U.K., and Stoltz B.M. J. Am. Chem. Soc. 127 (2005) 5340-5341
17. Tambar U.K., Ebner D.C., and Stoltz B.M. J. Am. Chem. Soc. 128 (2006) 11752-11753 C-P σ-bond:
18. Yoshida H., Watanabe M., Ohshita J., and Kunai A. Chem. Lett. 34 (2005) 1538-1539
19. For a review on insertion reactions of arynes into element-element σ-bonds, see:. Peña D., Pérez D., and Guitián E. Angew. Chem., Int. Ed. 45 (2006) 3579-3581
20. Three-component couplings of arynes were hitherto achieved using anionic nucleophiles in contrast to the results demonstrated herein:
21. Meyers A.I., and Pansegrau P.D. Tetrahedron Lett. 24 (1983) 4935-4938
22. Meyers A.I., and Pansegrau P.D. J. Chem. Soc., Chem. Commun. (1985) 690-691
23. Tripathy S., LeBlanc R., and Durst T. Org. Lett. 1 (1999) 1973-1975
24. Yoshida H., Fukushima H., Ohshita J., and Kunai A. Angew. Chem., Int. Ed. 43 (2004) 3935-3938
25. Yoshida H., Fukushima H., Ohshita J., and Kunai A. Tetrahedron Lett. 45 (2004) 8659-8662
26. Other three-component couplings using neutral nucleophiles:
27. Yoshida H., Watanabe M., Fukushima H., Ohshita J., and Kunai A. Org. Lett. 6 (2004) 4049-4051
28. Yoshida H., Fukushima H., Ohshita J., and Kunai A. J. Am. Chem. Soc. 128 (2006) 11040-11041
29. Jeganmohan M., and Cheng C.-H. Chem. Commun. (2006) 2454-2456
30. Three-component couplings of dimethyl acetylenedicarboxylate, isocyanides, and electrophiles have been reported:
31. Nair V., and Vinod A.U. Chem. Commun. (2000) 1019-1020
32. Nair V., Vinod A.U., and Rajesh C. J. Org. Chem. 66 (2001) 4427-4429
33. Nair V., Vinod A.U., Abhilash N., Menon R.S., Santhi V., Varma L.R., Viji S., Mathew S., and Srinivas R. Tetrahedron 59 (2003) 10279-10286
34. Nair V., Menon R.S., Beneesh P.B., Sreekumar V., and Bindu S. Org. Lett. 6 (2004) 767-769
35. Himeshima Y., Sonoda T., and Kobayashi H. Chem. Lett. (1983) 1211-1214
36. Although the three-component coupling product was elucidated to be a single isomer by NMR spectra, we could not determine the exact stereochemistry (E or Z) of the imine unit.
37. Diels-Alder reaction of thiophene with an aryne:. Callander D.D., Coe P.L., and Tatlow J.C. J. Chem. Soc., Chem. Commun. (1966) 143-144
38. Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 247264. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
39. Knorr R. Chem. Ber. 98 (1965) 4038-4039
40. Preferential nucleophilic attack at a para position of a chlorine atom also occurred in electrophilic coupling reactions of 4-chlorobenzyne:
41. Bunnett J.F., and Pyun C. J. Org. Chem. 34 (1969) 2035-2037
42. Bunnett J.F., and Kim J.K. J. Am. Chem. Soc. 95 (1973) 2254-2259
43. Similar regioselectivities were observed in other electrophilic coupling reactions of these unsymmetrical arynes. See Refs. 5,9b.
44. For the reversibility in the addition of nucleophiles to arynes, see Ref. 3.
45. The three-component coupling of benzyne with 2b and 7a at 0 °C proceeded much slower (47 h, 63% yield) than that with 3a (entry 3 of Table 2), showing lower reactivity of sulfonylimines in the three-component coupling.
46. Peña D., Pérez D., Guitián E., and Castedo L. J. Org. Chem. 65 (2000) 6944-6950
47. Yoshida H., Ikadai J., Shudo M., Ohshita J., and Kunai A. J. Am. Chem. Soc. 125 (2003) 6638-6639
48. Peña D., Pérez D., Guitián E., and Castedo L. J. Am. Chem. Soc. 121 (1999) 5827-5828
49. Peña D., Cobas A., Pérez D., and Guitián E. Synthesis (2002) 1454-1458
50. Yoshikawa E., Radhakrishnan K.V., and Yamamoto Y. J. Am. Chem. Soc. 122 (2000) 7280-7286
51. Yoshida H., Sugiura S., and Kunai A. Org. Lett. 4 (2002) 2767-2769
52. Ugi I., Meyr R., Lipinski M., Bodesheim F., and Rosendahl F. Org. Synth. 41 (1964) 13-15
53. Suginome M., Fukuda T., Nakamura H., and Ito Y. Organometallics 19 (2000) 719-721
54. Love B.E., Raje P.S., and Williams II T.C. Synlett (1994) 493-494