메뉴 건너뛰기




Volumn 127, Issue 2, 2005, Pages 605-613

Cp*RuCl-catalyzed [2 + 2 + 2] cycloadditions of α,ω- diynes with electron-deficient carbon-heteroatom multiple bonds leading to heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHLORINE; ELECTRONS; ISOMERS; NITRILE RESINS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

EID: 12944303660     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045694g     Document Type: Article
Times cited : (255)

References (73)
  • 3
    • 0000814758 scopus 로고
    • [2 + 2 + 2] Cycloadditions
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford
    • (a) Shore, N. E. [2 + 2 + 2] Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1129-1162.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1129-1162
    • Shore, N.E.1
  • 4
    • 0000134376 scopus 로고
    • Transition Metal Alkyne Complexes: Transition Metal-catalyzed Cyclotrimerization
    • Abel, E. W., Stone, F. G. A., Wilkinson, G. Hegedus, L. S., Eds.; Pergamon: Oxford
    • (b) Grotjahn, D. B. Transition Metal Alkyne Complexes: Transition Metal-catalyzed Cyclotrimerization. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G. Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 741-770.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 741-770
    • Grotjahn, D.B.1
  • 5
    • 0001119976 scopus 로고    scopus 로고
    • Cyclomerization of Alkynes
    • Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany
    • (c) Bönnemann, H.; Brijoux, W. Cyclomerization of Alkynes. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley: Weinheim, Germany, 1998; Vol. 1, pp 114-135.
    • (1998) Transition Metals for Organic Synthesis , vol.1 , pp. 114-135
    • Bönnemann, H.1    Brijoux, W.2
  • 7
    • 37049116387 scopus 로고
    • Wakatsuki, Y.; Yamazaki, H. J. Chem. Soc., Chem. Commun. 1973, 280. They reported that the reaction of a tetraphenylcobaltacyclopentadiene and methyl isothiocyanate gave a thiopyridone in 10% yield, but its structure was subsequently reassigned to a (2H)-thiopyran-2-imine (see Yamazaki, H. J. Synth. Org. Chem., Jpn. 1987, 45, 244-257).
    • (1973) J. Chem. Soc., Chem. Commun. , pp. 280
    • Wakatsuki, Y.1    Yamazaki, H.2
  • 8
    • 85004495566 scopus 로고
    • Wakatsuki, Y.; Yamazaki, H. J. Chem. Soc., Chem. Commun. 1973, 280. They reported that the reaction of a tetraphenylcobaltacyclopentadiene and methyl isothiocyanate gave a thiopyridone in 10% yield, but its structure was subsequently reassigned to a (2H)-thiopyran-2-imine (see Yamazaki, H. J. Synth. Org. Chem., Jpn. 1987, 45, 244-257).
    • (1987) J. Synth. Org. Chem., Jpn. , vol.45 , pp. 244-257
    • Yamazaki, H.1
  • 11
    • 0001503051 scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (1983) Transition Met. Chem. , vol.8 , pp. 250-252
    • Chiusoli, G.P.1    Pallini, L.2    Terenghi, G.3
  • 12
    • 45149147023 scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (1989) J. Organomet. Chem. , vol.363 , pp. 209-222
    • Battaglia, L.P.1    Delledonne, D.2    Nardelli, M.3    Predieri, G.4    Chiusoli, G.P.5    Costa, M.6    Pelizzi, C.7
  • 13
    • 0003013263 scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (1991) J. Organomet. Chem. , vol.417 , pp. 51-63
    • Zhou, Z.1    Battaglia, L.P.2    Chiusoli, G.P.3    Costa, M.4    Nardelli, M.5    Pelizzi, C.6    Predieri, G.7
  • 14
    • 0002135142 scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (1986) J. Organomet. Chem. , vol.307
    • Vitulli, G.1    Bertozzi, S.2    Lazzaroni, R.3    Salvadori, P.4
  • 15
    • 0002455536 scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (1987) J. Organomet. Chem. , vol.326
    • Vitulli, G.1    Bertozzi, S.2    Vignali, M.3    Lazzaroni, R.4    Salvadori, P.5
  • 16
    • 0034826606 scopus 로고    scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3157-3158
    • Moretto, A.F.1    Zhang, H.-C.2    Maryanoff, B.E.3
  • 17
    • 0036434027 scopus 로고    scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (2002) Chem. Commun. , pp. 2852-2853
    • Yong, L.1    Butenschön, H.2
  • 18
    • 1842781683 scopus 로고    scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 3489-3491
    • Hoshi, T.1    Katano, M.2    Nozawa, E.3    Suzuki, T.4    Hagiwara, H.5
  • 19
    • 4544286694 scopus 로고    scopus 로고
    • Other examples of the cycloaddition of α,ω-diynes with nitriles: (a) Chiusoli, G. P.; Pallini, L.; Terenghi, G. Transition Met. Chem. 1983, 8, 250-252. (b) Battaglia, L. P.; Delledonne, D.; Nardelli, M.; Predieri, G.; Chiusoli, G. P.; Costa, M.; Pelizzi, C. J. Organomet. Chem. 1989, 363, 209-222. (c) Zhou, Z.; Battaglia, L. P.; Chiusoli, G. P.; Costa, M.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1991, 417, 51-63. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1986, 307, C35-C37. (e) Vitulli, G.; Bertozzi, S.; Vignali, M.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1987, 326, C33-C36. (f) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158. (g) Yong, L.; Butenschön, H. Chem. Commun. 2002, 2852-2853. (h) Hoshi, T.; Katano, M.; Nozawa, E.; Suzuki, T.; Hagiwara, H. Tetrahedron Lett. 2004, 45, 3489-3491. (i) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3795-3797
    • Gutnov, A.1    Heller, B.2    Fischer, C.3    Drexler, H.-J.4    Spannenberg, A.5    Sundermann, B.6    Sundermann, C.7
  • 35
    • 4544240649 scopus 로고    scopus 로고
    • Recent examples, see (a) Bonaga, L. V. R.; Zhang, H.-C.; Gauthier, D. A.; Reddy, I.; Maryanoff, B. E. Org. Lett. 2003, 5, 4537-4540. (b) Duong, H. A.; Cross, M. J.; Louie, J. J. Am. Chem. Soc. 2004, 126, 11438-11439.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11438-11439
    • Duong, H.A.1    Cross, M.J.2    Louie, J.3
  • 36
    • 0035927877 scopus 로고    scopus 로고
    • Preliminary results have been reported: (a) Yamamoto, Y.; Okuda, S.; Itoh, K. Chem. Commun. 2001, 1102-1103. (b) Yamamoto, Y.; Takasishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117-2119. (c) Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 28-29.
    • (2001) Chem. Commun. , pp. 1102-1103
    • Yamamoto, Y.1    Okuda, S.2    Itoh, K.3
  • 37
    • 0000110406 scopus 로고    scopus 로고
    • Preliminary results have been reported: (a) Yamamoto, Y.; Okuda, S.; Itoh, K. Chem. Commun. 2001, 1102-1103. (b) Yamamoto, Y.; Takasishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117-2119. (c) Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 28-29.
    • (2001) Org. Lett. , vol.3 , pp. 2117-2119
    • Yamamoto, Y.1    Takasishi, H.2    Itoh, K.3
  • 38
    • 0037045249 scopus 로고    scopus 로고
    • Preliminary results have been reported: (a) Yamamoto, Y.; Okuda, S.; Itoh, K. Chem. Commun. 2001, 1102-1103. (b) Yamamoto, Y.; Takasishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117-2119. (c) Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 28-29.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 28-29
    • Yamamoto, Y.1    Takagishi, H.2    Itoh, K.3
  • 40
  • 46
  • 47
    • 0001184378 scopus 로고
    • and references therein
    • Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, 3087-3128, and references therein.
    • (1982) Tetrahedron , vol.38 , pp. 3087-3128
    • Weinreb, S.M.1    Staib, R.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.