Palladium-catalyzed enyne-yne [4 + 2] benzannulation as a new and general approach to polysubstituted benzenes

Journal of Organometallic Chemistry

Volumn 576, Issue 1-2, 1999, Pages 232-247

  Gevorgyan, Vladimir ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkynes; Benzene; Cycloaddition; Diynes; Enynes; Palladium

Indexed keywords

EID: 0001752763     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)01061-4     Document Type: Review

References (96)

1. M.C. Berthelot, R. Acad. Sci. 62 (1866) 905.
2. W. Reppe, O. Schlichting, K. Klager, T. Toepel, Justus Liebigs Ann. Chem. 560 (1948) 1.
3. (a) L.S. Meriwether, E.C. Clothup, G.W. Kennerly, R.N. Reusch, J. Org. Chem. 26 (1961) 5155.
4. (b) V.O. Reikhstel'd, K.L. Makovetskii, Russ. Chem. Rev. 35 (1966) 510.
5. For recent reviews, see: (a) K.P.C. Vollhardt, Angew. Chem. Int. Ed. Engl. 23 (1984) 539. (b) N.B. Schore, Chem. Rev. 88 (1988) 1081. (c) B.M. Trost, Science 254 (1991) 1471. (d) M. Lautens, W. Klute, W. Tam, Chem. Rev. 96 (1996) 49.
6. For recent reviews, see: (a) K.P.C. Vollhardt, Angew. Chem. Int. Ed. Engl. 23 (1984) 539. (b) N.B. Schore, Chem. Rev. 88 (1988) 1081. (c) B.M. Trost, Science 254 (1991) 1471. (d) M. Lautens, W. Klute, W. Tam, Chem. Rev. 96 (1996) 49.
7. For recent reviews, see: (a) K.P.C. Vollhardt, Angew. Chem. Int. Ed. Engl. 23 (1984) 539. (b) N.B. Schore, Chem. Rev. 88 (1988) 1081. (c) B.M. Trost, Science 254 (1991) 1471. (d) M. Lautens, W. Klute, W. Tam, Chem. Rev. 96 (1996) 49.
8. For recent reviews, see: (a) K.P.C. Vollhardt, Angew. Chem. Int. Ed. Engl. 23 (1984) 539. (b) N.B. Schore, Chem. Rev. 88 (1988) 1081. (c) B.M. Trost, Science 254 (1991) 1471. (d) M. Lautens, W. Klute, W. Tam, Chem. Rev. 96 (1996) 49.
9. See, for example: (a) J.P. Colman, J.W. Kang, W.F. Little, M.F. Sullivan, Inorg. Chem. 7 (1968) 1298. (b) R.A. Ferreri, A.P. Wolf, J. Phys. Chem. 88 (1984) 2256. (c) A. Borrini, P. Diversi, G. Ingrosso, A. Lucherini, G. Serra, J. Mol. Catal. 30 (1985) 181. (d) H. Yasuda, A. Nakamura, Rev. Chem. Intermed. 6 (1986) 365.
10. See, for example: (a) J.P. Colman, J.W. Kang, W.F. Little, M.F. Sullivan, Inorg. Chem. 7 (1968) 1298. (b) R.A. Ferreri, A.P. Wolf, J. Phys. Chem. 88 (1984) 2256. (c) A. Borrini, P. Diversi, G. Ingrosso, A. Lucherini, G. Serra, J. Mol. Catal. 30 (1985) 181. (d) H. Yasuda, A. Nakamura, Rev. Chem. Intermed. 6 (1986) 365.
11. See, for example: (a) J.P. Colman, J.W. Kang, W.F. Little, M.F. Sullivan, Inorg. Chem. 7 (1968) 1298. (b) R.A. Ferreri, A.P. Wolf, J. Phys. Chem. 88 (1984) 2256. (c) A. Borrini, P. Diversi, G. Ingrosso, A. Lucherini, G. Serra, J. Mol. Catal. 30 (1985) 181. (d) H. Yasuda, A. Nakamura, Rev. Chem. Intermed. 6 (1986) 365.
12. See, for example: (a) J.P. Colman, J.W. Kang, W.F. Little, M.F. Sullivan, Inorg. Chem. 7 (1968) 1298. (b) R.A. Ferreri, A.P. Wolf, J. Phys. Chem. 88 (1984) 2256. (c) A. Borrini, P. Diversi, G. Ingrosso, A. Lucherini, G. Serra, J. Mol. Catal. 30 (1985) 181. (d) H. Yasuda, A. Nakamura, Rev. Chem. Intermed. 6 (1986) 365.
13. (a) S.H. Lecker, N.H. Nguen, K.P.C. Vollhardt, J. Am. Chem. Soc. 108 (1986) 856.
14. (b) E. Negishi, L.S. Harring, Z. Owczarczyk, M.M. Mohamud, M. Ay, Tetrahedron Lett. 33 (1992) 3253.
15. (c) For earlier works see also [4a] and references therein.
16. See for example: (a) R.L. Halterman, N.H. Nguyen, K.P.C. Vollhardt, J. Am. Chem. Soc. 107 (1985) 1379. (b) B.C. Berris, G.H. Hovakeemian, Y.-H. Lai, H. Mestdagh, K.P.C. Vollhardt, J. Am. Chem. Soc. 107 (1985) 5670. (c) H.E. Kelson, K.P.C. Vollhardt, Z.-Y. Yang, Angew. Chem. Int. Ed. Engl. 24 (1985) 114. (d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 23 (1982) 2691.
17. See for example: (a) R.L. Halterman, N.H. Nguyen, K.P.C. Vollhardt, J. Am. Chem. Soc. 107 (1985) 1379. (b) B.C. Berris, G.H. Hovakeemian, Y.-H. Lai, H. Mestdagh, K.P.C. Vollhardt, J. Am. Chem. Soc. 107 (1985) 5670. (c) H.E. Kelson, K.P.C. Vollhardt, Z.-Y. Yang, Angew. Chem. Int. Ed. Engl. 24 (1985) 114. (d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 23 (1982) 2691.
18. See for example: (a) R.L. Halterman, N.H. Nguyen, K.P.C. Vollhardt, J. Am. Chem. Soc. 107 (1985) 1379. (b) B.C. Berris, G.H. Hovakeemian, Y.-H. Lai, H. Mestdagh, K.P.C. Vollhardt, J. Am. Chem. Soc. 107 (1985) 5670. (c) H.E. Kelson, K.P.C. Vollhardt, Z.-Y. Yang, Angew. Chem. Int. Ed. Engl. 24 (1985) 114. (d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 23 (1982) 2691.
19. See for example: (a) R.L. Halterman, N.H. Nguyen, K.P.C. Vollhardt, J. Am. Chem. Soc. 107 (1985) 1379. (b) B.C. Berris, G.H. Hovakeemian, Y.-H. Lai, H. Mestdagh, K.P.C. Vollhardt, J. Am. Chem. Soc. 107 (1985) 5670. (c) H.E. Kelson, K.P.C. Vollhardt, Z.-Y. Yang, Angew. Chem. Int. Ed. Engl. 24 (1985) 114. (d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 23 (1982) 2691.
20. S. Saito, M.M. Salter, V. Gevorgyan, N. Tsuboya, K. Tando, Y. Yamamoto, J. Am. Chem. Soc. 118 (1996) 3970.
21. For review, see: (a) E.R. Moore (Ed.), Styrene Polymers in Encyclopedia of Polymer Science and Engineering, 2nd ed. Vol. 16, Wiley Interscience, New york, 1989; and references therein. See also (b) K. Matyajaszewski (Ed.), Cationic Polymerizations: Mechanisms, Synthesis, and Applications, Marcel Dekker, New York, 1996. For an earlier review see: (c) R.H. Boundy, R.F. Boyer, Styrene, Its Polymers, Copolymers, and Derivatives, Reinhold, New York, 1952. For example of recent work, see: (d) B.R. Stranix, J.P. Gao, R. Barghi, J. Salha, J. Org. Chem. 62 (1997) 8987, and references therein.
22. For review, see: (a) E.R. Moore (Ed.), Styrene Polymers in Encyclopedia of Polymer Science and Engineering, 2nd ed. Vol. 16, Wiley Interscience, New york, 1989; and references therein. See also (b) K. Matyajaszewski (Ed.), Cationic Polymerizations: Mechanisms, Synthesis, and Applications, Marcel Dekker, New York, 1996. For an earlier review see: (c) R.H. Boundy, R.F. Boyer, Styrene, Its Polymers, Copolymers, and Derivatives, Reinhold, New York, 1952. For example of recent work, see: (d) B.R. Stranix, J.P. Gao, R. Barghi, J. Salha, J. Org. Chem. 62 (1997) 8987, and references therein.
23. For review, see: (a) E.R. Moore (Ed.), Styrene Polymers in Encyclopedia of Polymer Science and Engineering, 2nd ed. Vol. 16, Wiley Interscience, New york, 1989; and references therein. See also (b) K. Matyajaszewski (Ed.), Cationic Polymerizations: Mechanisms, Synthesis, and Applications, Marcel Dekker, New York, 1996. For an earlier review see: (c) R.H. Boundy, R.F. Boyer, Styrene, Its Polymers, Copolymers, and Derivatives, Reinhold, New York, 1952. For example of recent work, see: (d) B.R. Stranix, J.P. Gao, R. Barghi, J. Salha, J. Org. Chem. 62 (1997) 8987, and references therein.
24. For review, see: (a) E.R. Moore (Ed.), Styrene Polymers in Encyclopedia of Polymer Science and Engineering, 2nd ed. Vol. 16, Wiley Interscience, New york, 1989; and references therein. See also (b) K. Matyajaszewski (Ed.), Cationic Polymerizations: Mechanisms, Synthesis, and Applications, Marcel Dekker, New York, 1996. For an earlier review see: (c) R.H. Boundy, R.F. Boyer, Styrene, Its Polymers, Copolymers, and Derivatives, Reinhold, New York, 1952. For example of recent work, see: (d) B.R. Stranix, J.P. Gao, R. Barghi, J. Salha, J. Org. Chem. 62 (1997) 8987, and references therein.
25. See for example: (a) N. Nomura, J. Jin, H. Park, T.V. Rajan-Babu, J. Am. Chem. Soc. 120 (1998) 459. (b) S.P. Kolis, M.D. Chordia, R. Liu, M.E. Kopach, W.D. Harman, J. Am. Chem. Soc. 120 (1998) 2218. (c) S.K. Deb, T.M. Maddux, L. Yu, J. Am. Chem. Soc. 119 (1997) 9079. (d) A. Nzeru, J.R. Ebdon, S. Rimmer, J. Am. Chem. Soc. 119 (1997) 8928. (e) E. Galardon, S. Roue, P. Maux, G. Simonneaux, Tetrahedron Lett. 39 (1998) 2333. (f) R. Bruckner, R. Huisgen, J. Schmid, Tetrahedron Lett. 31 (1990) 7129.
26. See for example: (a) N. Nomura, J. Jin, H. Park, T.V. Rajan- Babu, J. Am. Chem. Soc. 120 (1998) 459. (b) S.P. Kolis, M.D. Chordia, R. Liu, M.E. Kopach, W.D. Harman, J. Am. Chem. Soc. 120 (1998) 2218. (c) S.K. Deb, T.M. Maddux, L. Yu, J. Am. Chem. Soc. 119 (1997) 9079. (d) A. Nzeru, J.R. Ebdon, S. Rimmer, J. Am. Chem. Soc. 119 (1997) 8928. (e) E. Galardon, S. Roue, P. Maux, G. Simonneaux, Tetrahedron Lett. 39 (1998) 2333. (f) R. Bruckner, R. Huisgen, J. Schmid, Tetrahedron Lett. 31 (1990) 7129.
27. See for example: (a) N. Nomura, J. Jin, H. Park, T.V. Rajan- Babu, J. Am. Chem. Soc. 120 (1998) 459. (b) S.P. Kolis, M.D. Chordia, R. Liu, M.E. Kopach, W.D. Harman, J. Am. Chem. Soc. 120 (1998) 2218. (c) S.K. Deb, T.M. Maddux, L. Yu, J. Am. Chem. Soc. 119 (1997) 9079. (d) A. Nzeru, J.R. Ebdon, S. Rimmer, J. Am. Chem. Soc. 119 (1997) 8928. (e) E. Galardon, S. Roue, P. Maux, G. Simonneaux, Tetrahedron Lett. 39 (1998) 2333. (f) R. Bruckner, R. Huisgen, J. Schmid, Tetrahedron Lett. 31 (1990) 7129.
28. See for example: (a) N. Nomura, J. Jin, H. Park, T.V. Rajan- Babu, J. Am. Chem. Soc. 120 (1998) 459. (b) S.P. Kolis, M.D. Chordia, R. Liu, M.E. Kopach, W.D. Harman, J. Am. Chem. Soc. 120 (1998) 2218. (c) S.K. Deb, T.M. Maddux, L. Yu, J. Am. Chem. Soc. 119 (1997) 9079. (d) A. Nzeru, J.R. Ebdon, S. Rimmer, J. Am. Chem. Soc. 119 (1997) 8928. (e) E. Galardon, S. Roue, P. Maux, G. Simonneaux, Tetrahedron Lett. 39 (1998) 2333. (f) R. Bruckner, R. Huisgen, J. Schmid, Tetrahedron Lett. 31 (1990) 7129.
29. See for example: (a) N. Nomura, J. Jin, H. Park, T.V. Rajan- Babu, J. Am. Chem. Soc. 120 (1998) 459. (b) S.P. Kolis, M.D. Chordia, R. Liu, M.E. Kopach, W.D. Harman, J. Am. Chem. Soc. 120 (1998) 2218. (c) S.K. Deb, T.M. Maddux, L. Yu, J. Am. Chem. Soc. 119 (1997) 9079. (d) A. Nzeru, J.R. Ebdon, S. Rimmer, J. Am. Chem. Soc. 119 (1997) 8928. (e) E. Galardon, S. Roue, P. Maux, G. Simonneaux, Tetrahedron Lett. 39 (1998) 2333. (f) R. Bruckner, R. Huisgen, J. Schmid, Tetrahedron Lett. 31 (1990) 7129.
30. See for example: (a) N. Nomura, J. Jin, H. Park, T.V. Rajan- Babu, J. Am. Chem. Soc. 120 (1998) 459. (b) S.P. Kolis, M.D. Chordia, R. Liu, M.E. Kopach, W.D. Harman, J. Am. Chem. Soc. 120 (1998) 2218. (c) S.K. Deb, T.M. Maddux, L. Yu, J. Am. Chem. Soc. 119 (1997) 9079. (d) A. Nzeru, J.R. Ebdon, S. Rimmer, J. Am. Chem. Soc. 119 (1997) 8928. (e) E. Galardon, S. Roue, P. Maux, G. Simonneaux, Tetrahedron Lett. 39 (1998) 2333. (f) R. Bruckner, R. Huisgen, J. Schmid, Tetrahedron Lett. 31 (1990) 7129.
31. For a review see: (a) R.F. Boyer, in: H.F. Mark, N.G. Gaylord, N.M. Bikales (Eds.), Encyclopedia of Polymer Science and Technology. Vol. 13, Wiley Interscience, New York, 1970. (b) A. Ravve, Principles of Polymer Chemistry, Plenum Press, New York, 1995, and references therein. For earlier examples, see: (c) W.Y. Lau, C.M. Burns, Can. J. Chem. 47 (1969) 2057. (d) H. Hopf, F. Lochner, Macromol. Chem. 84 (1965) 261. (e) V.V. Korshak, N.G. Matveeva, Bull. Acad. Sci. USSR Div. Chem. Sci. Engl. Transl. (1953) 547.
32. For a review see: (a) R.F. Boyer, in: H.F. Mark, N.G. Gaylord, N.M. Bikales (Eds.), Encyclopedia of Polymer Science and Technology. Vol. 13, Wiley Interscience, New York, 1970. (b) A. Ravve, Principles of Polymer Chemistry, Plenum Press, New York, 1995, and references therein. For earlier examples, see: (c) W.Y. Lau, C.M. Burns, Can. J. Chem. 47 (1969) 2057. (d) H. Hopf, F. Lochner, Macromol. Chem. 84 (1965) 261. (e) V.V. Korshak, N.G. Matveeva, Bull. Acad. Sci. USSR Div. Chem. Sci. Engl. Transl. (1953) 547.
33. For a review see: (a) R.F. Boyer, in: H.F. Mark, N.G. Gaylord, N.M. Bikales (Eds.), Encyclopedia of Polymer Science and Technology. Vol. 13, Wiley Interscience, New York, 1970. (b) A. Ravve, Principles of Polymer Chemistry, Plenum Press, New York, 1995, and references therein. For earlier examples, see: (c) W.Y. Lau, C.M. Burns, Can. J. Chem. 47 (1969) 2057. (d) H. Hopf, F. Lochner, Macromol. Chem. 84 (1965) 261. (e) V.V. Korshak, N.G. Matveeva, Bull. Acad. Sci. USSR Div. Chem. Sci. Engl. Transl. (1953) 547.
34. For a review see: (a) R.F. Boyer, in: H.F. Mark, N.G. Gaylord, N.M. Bikales (Eds.), Encyclopedia of Polymer Science and Technology. Vol. 13, Wiley Interscience, New York, 1970. (b) A. Ravve, Principles of Polymer Chemistry, Plenum Press, New York, 1995, and references therein. For earlier examples, see: (c) W.Y. Lau, C.M. Burns, Can. J. Chem. 47 (1969) 2057. (d) H. Hopf, F. Lochner, Macromol. Chem. 84 (1965) 261. (e) V.V. Korshak, N.G. Matveeva, Bull. Acad. Sci. USSR Div. Chem. Sci. Engl. Transl. (1953) 547.
35. For a review see: (a) R.F. Boyer, in: H.F. Mark, N.G. Gaylord, N.M. Bikales (Eds.), Encyclopedia of Polymer Science and Technology. Vol. 13, Wiley Interscience, New York, 1970. (b) A. Ravve, Principles of Polymer Chemistry, Plenum Press, New York, 1995, and references therein. For earlier examples, see: (c) W.Y. Lau, C.M. Burns, Can. J. Chem. 47 (1969) 2057. (d) H. Hopf, F. Lochner, Macromol. Chem. 84 (1965) 261. (e) V.V. Korshak, N.G. Matveeva, Bull. Acad. Sci. USSR Div. Chem. Sci. Engl. Transl. (1953) 547.
36. (a) S.A. Hardinger, C. Bayne, E. Kantorowski, R. McClellan, L. Larres, M.-A. Nuesse, J. Org. Chem. 60 (1995) 1104.
37. (b) T.J. Kwok, D.J. Wink, Organometallics 12 (1993) 1954.
38. (c) K. Srinivasan, P. Michaud, J.K. Kochi, J. Am. Chem. Soc. 108 (1986) 2309.
39. (d) M.H. Chisholm, C.E. Hammond, D. Ho, J.C. Huffman, J. Am. Chem. Soc. 108 (1986) 7860.
40. (e) J.P. Collman, P.D. Hampton, J.I. Brauman, J. Am. Chem. Soc. 112 (1990) 2986.
41. (f) R.H. Crabtree, M.F. Mellea, J.M. Quirk, J. Am. Chem. Soc. 106 (1984) 2913.
42. (g) A.L. Lyons, N. Turro, J. Am. Chem. Soc. 100 (1978) 3177.
43. (h) H. Coutelle, R. Huttel, J. Organomet. Chem. 153 (1978) 359.
44. (a) J.M. Saa, G. Martorell, A. Garsia-Raso, J. Org. Chem. 57 (1992) 678.
45. (b) G. Martorell, A. Garsia-Raso, J.M. Saa, Tetrahedron Lett. 31 (1990) 2357.
46. (c) L.H. Schwartzman, B.B. Corson, J. Am. Chem. Soc. 76 (1954) 781.
47. (d) See also ref [4f].
48. Very recently an elegant method for the preparation of 2,6-disubstituted styrenes was reported, however this method was restricted to the preparation of styrenes which neccessarily possess an additional substituent at the β-position. M. Catelani, F. Frignani, A. Rangoni, Angew. Chem. Int. Ed. Engl. 36 (1997) 119.
49. V. Gevorgyan, K. Tando, N. Uchiyama, Y. Yamamoto, J. Org. Chem. 63 (1998) 7022.
50. S. Saito, N. Tsuboya, Y. Yamamoto, J. Org. Chem. 62 (1997) 5042.
51. P.A.A. Klusener, W. Kulik, L. Brandsma, J. Org. Chem. 52 (1987) 5261.
52. For recent reviews on synthesis of cyclophanes, see: (a) Top. Curr. Chem. 172; E. Weber (Ed.), Springer-Verlag, Berlin, 1994. (b) F. Vögtle (Ed.), Cyclophane Chemistry, Willey, Chichester, 1993. (c) F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, 1991.
53. For recent reviews on synthesis of cyclophanes, see: (a) Top. Curr. Chem. 172; E. Weber (Ed.), Springer-Verlag, Berlin, 1994. (b) F. Vögtle (Ed.), Cyclophane Chemistry, Willey, Chichester, 1993. (c) F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, 1991.
54. For recent reviews on synthesis of cyclophanes, see: (a) Top. Curr. Chem. 172; E. Weber (Ed.), Springer-Verlag, Berlin, 1994. (b) F. Vögtle (Ed.), Cyclophane Chemistry, Willey, Chichester, 1993. (c) F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, 1991.
55. It is generally accepted that alkylation of substrates bearing a ß-alkoxy functionality is difficult due to the electron-withdrawing nature of the β-oxygen. For a review see: A. Streitwieser, Solvolytic Displacement Reactions, McGraw-Hill, New York, 1962, pp. 16-18.
56. Direct nucleophilic alkylation at the carbon center of triflates bearing a β-oxygen atom has been reported. For a review on alkylations with organocuprate reagents see for example: (a) B.H. Lipshutz, Synthesis (1987) 325. For alkylations with Grignard reagents see: (b) H. Kotsuki, I. Kadota, M. Ochi, Tetrahedron Lett. 30 (1989) 1281.
57. Direct nucleophilic alkylation at the carbon center of triflates bearing a β-oxygen atom has been reported. For a review on alkylations with organocuprate reagents see for example: (a) B.H. Lipshutz, Synthesis (1987) 325. For alkylations with Grignard reagents see: (b) H. Kotsuki, I. Kadota, M. Ochi, Tetrahedron Lett. 30 (1989) 1281.
58. D. Weibel, V. Gevorgyan, Y. Yamamoto, J. Org. Chem. 63 (1998) 1217.
59. H. Kotsuki, I. Kadota, M. Ochi, Tetrahedron Lett. 31 (1990) 4609.
60. For regioselective epoxide ring openings with acetylides in the presence of metal salts, see: M. Chini, P. Crotti, L. Favero, F. Macchia, Tetrahedron Lett. 32 (1991) 6617.
61. A template-directed effect of alkali metal salts in the ruthenium-catalyzed ring-closure metathesis has been recently demonstrated see: M.J. Marsella, H.D. Maynard, R.H. Grubbs, Angew. Chem. Int. Ed. Engl. 36 (1997) 1101.
62. It was also found that 2,4-disubstituted enynes do not undergo intermolecular homo-benzannulation under the mentioned reaction conditions, see Ref. [29].
63. Although scattered data on related processes such as thermal (a, b) or Lewis acid mediated (a) intramolecular enyne-yne [4 + 2] cycloaddition reaction were recently reported, the more synthetically useful intermolecular enyne-yne cross-benzannulation still remained unemployed. (a) R.L. Danheiser, A.E. Gould, R. Fernandez de la Predilla, A.L. Helgason, J. Org. Chem. 59 (1994) 5514. (b) R.C. Burrell, K.J. Daoust, A.Z. Bradley, K.J. DiRico, R.P. Johnson, J. Am. Chem. Soc. 118 (1996) 4218.
64. Although scattered data on related processes such as thermal (a, b) or Lewis acid mediated (a) intramolecular enyne-yne [4 + 2] cycloaddition reaction were recently reported, the more synthetically useful intermolecular enyne-yne cross-benzannulation still remained unemployed. (a) R.L. Danheiser, A.E. Gould, R. Fernandez de la Predilla, A.L. Helgason, J. Org. Chem. 59 (1994) 5514. (b) R.C. Burrell, K.J. Daoust, A.Z. Bradley, K.J. DiRico, R.P. Johnson, J. Am. Chem. Soc. 118 (1996) 4218.
65. The structure of para -oriented 22 was unambiguously confirmed by 500 MHz NOE- and COLOC NMR analyses.
66. V. Gevorgyan, A. Takeda, Y. Yamamoto, J. Am. Chem. Soc. 119 (1997) 11313.
67. The excess of enyne 1a underwent homo-dimerization, affording 2, see also footnote c, Table 4.
68. V. Gevorgyan, A. Takeda, M. Honma, N. Sadayori, Y. Yamamoto (manuscript in preparation).
69. V. Gevorgyan, N. Sadayori, Y. Yamamoto, Tetrahedron Lett. 38 (1997) 8603.
70. (a) X. Yang, W. Jiang, C.B. Knobler, M.F. Hawthorne, J. Am. Chem. Soc. 114 (1992) 9719.
71. (b) J. Müller, K. Base, T.F. Magnera, J. Michl, J. Am. Chem. Soc. 114 (1992) 9721.
72. W. Clegg, W.R. Gill, J.A.H. MacBride, Angew. Chem. Int. Ed. Engl. 32 (1993) 1328.
73. U. Schöberl, T.F. Magnera, R.M. Harrison, F. Fleicher, J.L. Pflug, P.F.H. Schwab, X. Meng, D. Lopiak, B.C. Noll, V.S. Allured, T. Rudalevige, S. Lee, J. Michl, J. Am. Chem. Soc. 119 (1997) 3907.
74. V. Gevorgyan, Y.-H. Kim, N. Sadayori, Y. Yamamoto (manuscript in preparation).
75. For a general review, see: (a) D.A. Whiting, in: J.F. Stoddart (Ed.), Comprehensive Organic Chemistry. Vol. 1, Pergamon Press, Oxford, 1979, Ch. 4.2. For a review on aryl C-O bond-forming reactions, see: (b) C.K.-F. Chiu, in: A.R. Katritzky, O. Meth-Cohn, C.W. Rees (Eds.), Comprehensive Organic Functional Group Transformations. Vol. 2, Pergamon Press, New York, 1995, Ch. 2.13.
76. For a general review, see: (a) D.A. Whiting, in: J.F. Stoddart (Ed.), Comprehensive Organic Chemistry. Vol. 1, Pergamon Press, Oxford, 1979, Ch. 4.2. For a review on aryl C-O bond- forming reactions, see: (b) C.K.-F. Chiu, in: A.R. Katritzky, O. Meth-Cohn, C.W. Rees (Eds.), Comprehensive Organic Functional Group Transformations. Vol. 2, Pergamon Press, New York, 1995, Ch. 2.13.
77. For reviews, see: (a) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis. Vol. 5, Pergamon Press, New York, 1991, p. 1065. (b) N.E. Schore, Chem. Rev. 88 (1988) 1081. See also: (c) C.A. Merlic, D. Xu, J. Am. Chem. Soc. 113 (1991) 7418. (d) P. Turnbull, M.J. Heilman, H.W. Moore, J. Org. Chem. 61 (1996) 2584. (e) S.H. Koo, L.S. Liebeskind, J. Am. Chem. Soc. 117 (1995) 3389. (f) A. Covarrubias-Zúñiga, E. Ríos-Barrios, J. Org. Chem. 62 (1997) 5688. (g) D. Collomb, A. Doutheau, Tetrahedron Lett. 38 (1997) 1397. (h) J. Barluenga, A. Refnández-Acebes, A.A. Trabanco, J. Flórez, J. Am. Chem. Soc. 119 (1997) 7591.
78. For reviews, see: (a) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis. Vol. 5, Pergamon Press, New York, 1991, p. 1065. (b) N.E. Schore, Chem. Rev. 88 (1988) 1081. See also: (c) C.A. Merlic, D. Xu, J. Am. Chem. Soc. 113 (1991) 7418. (d) P. Turnbull, M.J. Heilman, H.W. Moore, J. Org. Chem. 61 (1996) 2584. (e) S.H. Koo, L.S. Liebeskind, J. Am. Chem. Soc. 117 (1995) 3389. (f) A. Covarrubias-Zúñiga, E. Ríos-Barrios, J. Org. Chem. 62 (1997) 5688. (g) D. Collomb, A. Doutheau, Tetrahedron Lett. 38 (1997) 1397. (h) J. Barluenga, A. Refnández-Acebes, A.A. Trabanco, J. Flórez, J. Am. Chem. Soc. 119 (1997) 7591.
79. For reviews, see: (a) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis. Vol. 5, Pergamon Press, New York, 1991, p. 1065. (b) N.E. Schore, Chem. Rev. 88 (1988) 1081. See also: (c) C.A. Merlic, D. Xu, J. Am. Chem. Soc. 113 (1991) 7418. (d) P. Turnbull, M.J. Heilman, H.W. Moore, J. Org. Chem. 61 (1996) 2584. (e) S.H. Koo, L.S. Liebeskind, J. Am. Chem. Soc. 117 (1995) 3389. (f) A. Covarrubias-Zúñiga, E. Ríos-Barrios, J. Org. Chem. 62 (1997) 5688. (g) D. Collomb, A. Doutheau, Tetrahedron Lett. 38 (1997) 1397. (h) J. Barluenga, A. Refnández-Acebes, A.A. Trabanco, J. Flórez, J. Am. Chem. Soc. 119 (1997) 7591.
80. For reviews, see: (a) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis. Vol. 5, Pergamon Press, New York, 1991, p. 1065. (b) N.E. Schore, Chem. Rev. 88 (1988) 1081. See also: (c) C.A. Merlic, D. Xu, J. Am. Chem. Soc. 113 (1991) 7418. (d) P. Turnbull, M.J. Heilman, H.W. Moore, J. Org. Chem. 61 (1996) 2584. (e) S.H. Koo, L.S. Liebeskind, J. Am. Chem. Soc. 117 (1995) 3389. (f) A. Covarrubias-Zúñiga, E. Ríos-Barrios, J. Org. Chem. 62 (1997) 5688. (g) D. Collomb, A. Doutheau, Tetrahedron Lett. 38 (1997) 1397. (h) J. Barluenga, A. Refnández-Acebes, A.A. Trabanco, J. Flórez, J. Am. Chem. Soc. 119 (1997) 7591.
81. For reviews, see: (a) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis. Vol. 5, Pergamon Press, New York, 1991, p. 1065. (b) N.E. Schore, Chem. Rev. 88 (1988) 1081. See also: (c) C.A. Merlic, D. Xu, J. Am. Chem. Soc. 113 (1991) 7418. (d) P. Turnbull, M.J. Heilman, H.W. Moore, J. Org. Chem. 61 (1996) 2584. (e) S.H. Koo, L.S. Liebeskind, J. Am. Chem. Soc. 117 (1995) 3389. (f) A. Covarrubias-Zúñiga, E. Ríos-Barrios, J. Org. Chem. 62 (1997) 5688. (g) D. Collomb, A. Doutheau, Tetrahedron Lett. 38 (1997) 1397. (h) J. Barluenga, A. Refnández-Acebes, A.A. Trabanco, J. Flórez, J. Am. Chem. Soc. 119 (1997) 7591.
82. For reviews, see: (a) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis. Vol. 5, Pergamon Press, New York, 1991, p. 1065. (b) N.E. Schore, Chem. Rev. 88 (1988) 1081. See also: (c) C.A. Merlic, D. Xu, J. Am. Chem. Soc. 113 (1991) 7418. (d) P. Turnbull, M.J. Heilman, H.W. Moore, J. Org. Chem. 61 (1996) 2584. (e) S.H. Koo, L.S. Liebeskind, J. Am. Chem. Soc. 117 (1995) 3389. (f) A. Covarrubias-Zúñiga, E. Ríos-Barrios, J. Org. Chem. 62 (1997) 5688. (g) D. Collomb, A. Doutheau, Tetrahedron Lett. 38 (1997) 1397. (h) J. Barluenga, A. Refnández-Acebes, A.A. Trabanco, J. Flórez, J. Am. Chem. Soc. 119 (1997) 7591.
83. For reviews, see: (a) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis. Vol. 5, Pergamon Press, New York, 1991, p. 1065. (b) N.E. Schore, Chem. Rev. 88 (1988) 1081. See also: (c) C.A. Merlic, D. Xu, J. Am. Chem. Soc. 113 (1991) 7418. (d) P. Turnbull, M.J. Heilman, H.W. Moore, J. Org. Chem. 61 (1996) 2584. (e) S.H. Koo, L.S. Liebeskind, J. Am. Chem. Soc. 117 (1995) 3389. (f) A. Covarrubias-Zúñiga, E. Ríos-Barrios, J. Org. Chem. 62 (1997) 5688. (g) D. Collomb, A. Doutheau, Tetrahedron Lett. 38 (1997) 1397. (h) J. Barluenga, A. Refnández-Acebes, A.A. Trabanco, J. Flórez, J. Am. Chem. Soc. 119 (1997) 7591.
84. For reviews, see: (a) W.D. Wulff, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis. Vol. 5, Pergamon Press, New York, 1991, p. 1065. (b) N.E. Schore, Chem. Rev. 88 (1988) 1081. See also: (c) C.A. Merlic, D. Xu, J. Am. Chem. Soc. 113 (1991) 7418. (d) P. Turnbull, M.J. Heilman, H.W. Moore, J. Org. Chem. 61 (1996) 2584. (e) S.H. Koo, L.S. Liebeskind, J. Am. Chem. Soc. 117 (1995) 3389. (f) A. Covarrubias-Zúñiga, E. Ríos-Barrios, J. Org. Chem. 62 (1997) 5688. (g) D. Collomb, A. Doutheau, Tetrahedron Lett. 38 (1997) 1397. (h) J. Barluenga, A. Refnández-Acebes, A.A. Trabanco, J. Flórez, J. Am. Chem. Soc. 119 (1997) 7591.
85. V. Gevorgyan, L.G. Quan, Y. Yamamoto, J. Org. Chem. 63 (1998) 1244.
86. V. Gevorgyan, L.G. Quan, Y. Yamamoto (manuscript in preparation).
87. G. Reginato, A. Mordini, A. Degl'Innocenti, M. Caracciolo, Tetyrahedron Lett. 36 (1995) 8275.
88. V. Gevorgyan, N. Tsuboya, Y. Yamamoto (manuscript in preparation).
89. π-Propargyl palladium complexes have been recently isolated and fully characterized. See: (a) S. Ogoshi, K. Tsutsumi, H. Kurosawa, J. Organomet. Chem. 493 (1995) C19. (b) S. Ogoshi, K. Tsutsumi, M. Ooi, H. Kurosawa, J. Am. Chem. Soc. 117 (1995) 10415.
90. π-Propargyl palladium complexes have been recently isolated and fully characterized. See: (a) S. Ogoshi, K. Tsutsumi, H. Kurosawa, J. Organomet. Chem. 493 (1995) C19. (b) S. Ogoshi, K. Tsutsumi, M. Ooi, H. Kurosawa, J. Am. Chem. Soc. 117 (1995) 10415.
91. The coordination of palladium to the propargyl group in the intermediate 72 is supported not only by the exclusive formation of a sole regioisomer 74 but also by the fact that simple alkynes, such as acetylene and its alkyl-, aryl-, halo-, and cyanoderivatives, which do not possess such an additional alkynyl group, do not act as enynophiles in the mentioned reaction. Accordingly, an alternative explanation of remarkable reactivity of diynes in terms of steric effects was discounted by the observation that acetylene itself did not act as an enynophile in that reaction.
92. This type of 6-membered strained cyclic cumulene has been recently proposed as an intermediate in the dehydro Diels-Alder cycloadditions. (a) For review see: R.P. Johnson, Chem. Rev. 89 (1989) 1111. (b) See also reference [26b].
93. This type of 6-membered strained cyclic cumulene has been recently proposed as an intermediate in the dehydro Diels-Alder cycloadditions. (a) For review see: R.P. Johnson, Chem. Rev. 89 (1989) 1111. (b) See also reference [26b].
94. V. Gevorgyan, U. Radhakrishnan, A. Takeda, Y. Yamamoto (manuscript in preparation).
95. 2, see: B.M. Trost, M.T. Sorum, C. Chan, A.E. Harms, G. Rühter, J. Am. Chem. Soc. 119 (1997) 698. For other transition metal-catalyzed alkyne dimerizations, see references therein.
96. 2-TDMPP catalyst system [46] no [4 + 2] benzannulation took place, although the dimerization of alkynes proceeded smoothly.