Regiospesific Synthesis of Polysubstituted Phenols via the Palladium-Catalyzed Enyne-Diyne [4 + 2] Cross-Benzannulation Pathway

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1244-1247

  Gevorgyan, Vladimir ^a   Quan, Long Guo ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001266390     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971817m     Document Type: Article

References (31)

1. - as nucleophiles in aromatic substitution, see: (d) The Chemistry of the Hydroxyl Group; Patai, S.; Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of phenols from aryl halides and aryl ethers, see: (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (g) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
2. - as nucleophiles in aromatic substitution, see: (d) The Chemistry of the Hydroxyl Group; Patai, S.; Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of phenols from aryl halides and aryl ethers, see: (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (g) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
3. - as nucleophiles in aromatic substitution, see: (d) The Chemistry of the Hydroxyl Group; Patai, S.; Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of phenols from aryl halides and aryl ethers, see: (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (g) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
4. - as nucleophiles in aromatic substitution, see: (d) The Chemistry of the Hydroxyl Group; Patai, S.; Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of phenols from aryl halides and aryl ethers, see: (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (g) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
5. - as nucleophiles in aromatic substitution, see: (d) The Chemistry of the Hydroxyl Group; Patai, S.; Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of phenols from aryl halides and aryl ethers, see: (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (g) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
6. - as nucleophiles in aromatic substitution, see: (d) The Chemistry of the Hydroxyl Group; Patai, S.; Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of phenols from aryl halides and aryl ethers, see: (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (g) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
7. - as nucleophiles in aromatic substitution, see: (d) The Chemistry of the Hydroxyl Group; Patai, S.; Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of phenols from aryl halides and aryl ethers, see: (e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (f) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (g) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
8. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, 1065. (b) Schore, N. E. Chem. Rev. (Washington, D.C.) 1988, 88, 1081-1119. See also: (c) Merlic, C. A.;Xu, D. J. Am. Chem. Soc. 1991, 113, 7418. Turnbull, P.; Heilman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584. (e) Koo, S. H.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389. (f) Covarrubias-Zúñiga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688. (g) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 1397. (h) Barluenga, J.; Refnández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591.
9. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, 1065. (b) Schore, N. E. Chem. Rev. (Washington, D.C.) 1988, 88, 1081-1119. See also: (c) Merlic, C. A.;Xu, D. J. Am. Chem. Soc. 1991, 113, 7418. Turnbull, P.; Heilman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584. (e) Koo, S. H.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389. (f) Covarrubias-Zúñiga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688. (g) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 1397. (h) Barluenga, J.; Refnández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591.
10. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, 1065. (b) Schore, N. E. Chem. Rev. (Washington, D.C.) 1988, 88, 1081-1119. See also: (c) Merlic, C. A.;Xu, D. J. Am. Chem. Soc. 1991, 113, 7418. Turnbull, P.; Heilman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584. (e) Koo, S. H.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389. (f) Covarrubias-Zúñiga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688. (g) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 1397. (h) Barluenga, J.; Refnández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591.
11. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, 1065. (b) Schore, N. E. Chem. Rev. (Washington, D.C.) 1988, 88, 1081-1119. See also: (c) Merlic, C. A.;Xu, D. J. Am. Chem. Soc. 1991, 113, 7418. Turnbull, P.; Heilman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584. (e) Koo, S. H.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389. (f) Covarrubias-Zúñiga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688. (g) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 1397. (h) Barluenga, J.; Refnández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591.
12. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, 1065. (b) Schore, N. E. Chem. Rev. (Washington, D.C.) 1988, 88, 1081-1119. See also: (c) Merlic, C. A.;Xu, D. J. Am. Chem. Soc. 1991, 113, 7418. Turnbull, P.; Heilman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584. (e) Koo, S. H.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389. (f) Covarrubias-Zúñiga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688. (g) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 1397. (h) Barluenga, J.; Refnández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591.
13. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, 1065. (b) Schore, N. E. Chem. Rev. (Washington, D.C.) 1988, 88, 1081-1119. See also: (c) Merlic, C. A.;Xu, D. J. Am. Chem. Soc. 1991, 113, 7418. Turnbull, P.; Heilman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584. (e) Koo, S. H.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389. (f) Covarrubias-Zúñiga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688. (g) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 1397. (h) Barluenga, J.; Refnández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591.
14. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, 1065. (b) Schore, N. E. Chem. Rev. (Washington, D.C.) 1988, 88, 1081-1119. See also: (c) Merlic, C. A.;Xu, D. J. Am. Chem. Soc. 1991, 113, 7418. Turnbull, P.; Heilman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584. (e) Koo, S. H.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389. (f) Covarrubias-Zúñiga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688. (g) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 1397. (h) Barluenga, J.; Refnández-Acebes, A.; Trabanco, A. A.; Flórez, J. J. Am. Chem. Soc. 1997, 119, 7591.
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19. 6 intramolecular enyne-yne [4 + 2] cycloaddition reactions were recently reported.
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22. 9 Furthermore, we did not succeed in isolating the siloxy-substituted enyne 1f and diyne 2d due to their low stability. Equation Presented.
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24. 11
25. Gevorgyan, V.; Tando, K.; Uchiyama, N.; Yamamoto, Y. Unpublished results.
26. 4b
27. 3 together with major cross-benzannulation product were produced. For some examples on chemospecific benzannulation of the alkyl- and aryl-substituted enynes, see ref 4b.
28. Alkoxy-substituted aromatics are ubiquitous structural units in biologically important molecules and thus are of great importance for synthetic organic chemistry. See, for example, ref 1b.
29. Recently, Merlic and co-worker have demonstrated an example of the construction of alkoxybenzene derivative via ruthenium-catalyzed intramolecular cyclization of dienylalkynes; see: Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319.
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