Synthesis of oxygen heterocycles via a pallidium-catalyzed C-O bond-forming reaction

Journal of the American Chemical Society

Volumn 118, Issue 42, 1996, Pages 10333-10334

  Palucki, Michael ^a   Wolfe, John P ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; BENZOPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029855494     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962408v     Document Type: Article

References (46)

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21. For a review of alkenyl and aryl C-O bond forming reactions see: (a) Chiuy, C. K.-F. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: New York, 1995: Vol. 2, Chapter 2.13. For the synthesis and application of benzopyrans see: (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984: Vol. 3, Chapter 2.24. For the synthesis and application of benzofurans see: (c) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 4, Chapter 3.12. For examples of nickel catalyzed synthesis of aryl ethers see: (d) Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267. (e) Cristau, H.-J.; Desmurs, J.-R. Ind. Chem. Libr. 1995, 7, 240.
22. For a review of alkenyl and aryl C-O bond forming reactions see: (a) Chiuy, C. K.-F. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: New York, 1995: Vol. 2, Chapter 2.13. For the synthesis and application of benzopyrans see: (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984: Vol. 3, Chapter 2.24. For the synthesis and application of benzofurans see: (c) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 4, Chapter 3.12. For examples of nickel catalyzed synthesis of aryl ethers see: (d) Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267. (e) Cristau, H.-J.; Desmurs, J.-R. Ind. Chem. Libr. 1995, 7, 240.
23. For a review of alkenyl and aryl C-O bond forming reactions see: (a) Chiuy, C. K.-F. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: New York, 1995: Vol. 2, Chapter 2.13. For the synthesis and application of benzopyrans see: (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984: Vol. 3, Chapter 2.24. For the synthesis and application of benzofurans see: (c) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 4, Chapter 3.12. For examples of nickel catalyzed synthesis of aryl ethers see: (d) Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267. (e) Cristau, H.-J.; Desmurs, J.-R. Ind. Chem. Libr. 1995, 7, 240.
24. For a review of alkenyl and aryl C-O bond forming reactions see: (a) Chiuy, C. K.-F. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: New York, 1995: Vol. 2, Chapter 2.13. For the synthesis and application of benzopyrans see: (b) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984: Vol. 3, Chapter 2.24. For the synthesis and application of benzofurans see: (c) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 4, Chapter 3.12. For examples of nickel catalyzed synthesis of aryl ethers see: (d) Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267. (e) Cristau, H.-J.; Desmurs, J.-R. Ind. Chem. Libr. 1995, 7, 240.
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33. In addition to tri-o-tolylphosphine, the following ligands were screened for the cyclization of substrate 1 and found to be ineffective: 1,-10-phenanthroline, 2,2′-dipyridyl, tris(2,4,6-trimethoxyphenyl)phosphine, 1,2-bis(diphenylphosophino)benzene, and 1,2-bis(diphenylphosphino)ethane.
34. 2 for any of the entries listed in Table 1.
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36. 4 in toluene affords upon heating the dehalogenated product and formaldehyde in high yields. (b) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619.
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41. It has not been determined if deprotonation occurs prior to or after oxygen coordination.
42. 3-allyl or C(O)Me) see: (a) Stanton, S. A.; Felman, S. W.; Parkhurst, C. S.; Godleski, S. A. J. Am. Chem. Soc. 1983, 105, 1964. (b) Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662. (c) Komiya, S.; Akia, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (d) Larock, R. C.; Berrios-Peña, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. For a review of the synthesis and reactivity of late transition metal alkoxides see: (e) Bryndza, H.; Tam, W. Chem. Rev. 1988, 88, 1163.
43. 3-allyl or C(O)Me) see: (a) Stanton, S. A.; Felman, S. W.; Parkhurst, C. S.; Godleski, S. A. J. Am. Chem. Soc. 1983, 105, 1964. (b) Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662. (c) Komiya, S.; Akia, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (d) Larock, R. C.; Berrios-Peña, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. For a review of the synthesis and reactivity of late transition metal alkoxides see: (e) Bryndza, H.; Tam, W. Chem. Rev. 1988, 88, 1163.
44. 3-allyl or C(O)Me) see: (a) Stanton, S. A.; Felman, S. W.; Parkhurst, C. S.; Godleski, S. A. J. Am. Chem. Soc. 1983, 105, 1964. (b) Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662. (c) Komiya, S.; Akia, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (d) Larock, R. C.; Berrios-Peña, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. For a review of the synthesis and reactivity of late transition metal alkoxides see: (e) Bryndza, H.; Tam, W. Chem. Rev. 1988, 88, 1163.
45. 3-allyl or C(O)Me) see: (a) Stanton, S. A.; Felman, S. W.; Parkhurst, C. S.; Godleski, S. A. J. Am. Chem. Soc. 1983, 105, 1964. (b) Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662. (c) Komiya, S.; Akia, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (d) Larock, R. C.; Berrios-Peña, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. For a review of the synthesis and reactivity of late transition metal alkoxides see: (e) Bryndza, H.; Tam, W. Chem. Rev. 1988, 88, 1163.
46. 3-allyl or C(O)Me) see: (a) Stanton, S. A.; Felman, S. W.; Parkhurst, C. S.; Godleski, S. A. J. Am. Chem. Soc. 1983, 105, 1964. (b) Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662. (c) Komiya, S.; Akia, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130. (d) Larock, R. C.; Berrios-Peña, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. For a review of the synthesis and reactivity of late transition metal alkoxides see: (e) Bryndza, H.; Tam, W. Chem. Rev. 1988, 88, 1163.