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Volumn 5, Issue 20, 2003, Pages 3659-3662

Iridium complex-catalyzed highly selective cross [2 + 2 + 2] cycloaddition of two different monoynes: 2:1 Coupling versus 1:2 coupling

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ETHANE; IRIDIUM; LIGAND;

EID: 0142074827     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035330d     Document Type: Article
Times cited : (86)

References (46)
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    • Stoichiometric reaction. For Zr, see: (a) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. For Ti, see: (b) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. Catalytic reaction. For Rh, see: (c) Abudulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103. For Pd, see: (d) Dieck, T. H.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243. For Ni, see: (e) Mori, N.; Ikeda, S.; Odashima, K. J. Chem. Soc., Chem. Commun. 2001, 181. Monoyne with allenes, see: (f) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233. Monoyne with allyl tosylates, see: (g) Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 2, 655. Monoyne with enones, see: (h) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 2722.
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    • Takahashi, T.1    Xi, Z.2    Yamazaki, A.3    Liu, Y.4    Nakajima, K.5    Kotora, M.6
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    • Stoichiometric reaction. For Zr, see: (a) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. For Ti, see: (b) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. Catalytic reaction. For Rh, see: (c) Abudulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103. For Pd, see: (d) Dieck, T. H.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243. For Ni, see: (e) Mori, N.; Ikeda, S.; Odashima, K. J. Chem. Soc., Chem. Commun. 2001, 181. Monoyne with allenes, see: (f) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233. Monoyne with allyl tosylates, see: (g) Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 2, 655. Monoyne with enones, see: (h) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 2722.
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    • Stoichiometric reaction. For Zr, see: (a) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. For Ti, see: (b) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. Catalytic reaction. For Rh, see: (c) Abudulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103. For Pd, see: (d) Dieck, T. H.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243. For Ni, see: (e) Mori, N.; Ikeda, S.; Odashima, K. J. Chem. Soc., Chem. Commun. 2001, 181. Monoyne with allenes, see: (f) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233. Monoyne with allyl tosylates, see: (g) Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 2, 655. Monoyne with enones, see: (h) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 2722.
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    • Stoichiometric reaction. For Zr, see: (a) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. For Ti, see: (b) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. Catalytic reaction. For Rh, see: (c) Abudulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103. For Pd, see: (d) Dieck, T. H.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243. For Ni, see: (e) Mori, N.; Ikeda, S.; Odashima, K. J. Chem. Soc., Chem. Commun. 2001, 181. Monoyne with allenes, see: (f) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233. Monoyne with allyl tosylates, see: (g) Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 2, 655. Monoyne with enones, see: (h) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 2722.
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    • Stoichiometric reaction. For Zr, see: (a) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. For Ti, see: (b) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. Catalytic reaction. For Rh, see: (c) Abudulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103. For Pd, see: (d) Dieck, T. H.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243. For Ni, see: (e) Mori, N.; Ikeda, S.; Odashima, K. J. Chem. Soc., Chem. Commun. 2001, 181. Monoyne with allenes, see: (f) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233. Monoyne with allyl tosylates, see: (g) Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 2, 655. Monoyne with enones, see: (h) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 2722.
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    • Mori, N.1    Ikeda, S.2    Odashima, K.3
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    • 0001226123 scopus 로고    scopus 로고
    • Stoichiometric reaction. For Zr, see: (a) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. For Ti, see: (b) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. Catalytic reaction. For Rh, see: (c) Abudulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103. For Pd, see: (d) Dieck, T. H.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243. For Ni, see: (e) Mori, N.; Ikeda, S.; Odashima, K. J. Chem. Soc., Chem. Commun. 2001, 181. Monoyne with allenes, see: (f) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233. Monoyne with allyl tosylates, see: (g) Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 2, 655. Monoyne with enones, see: (h) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 2722.
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    • Shanmugasundaram, M.1    Wu, M.-S.2    Cheng, C.-H.3
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    • Stoichiometric reaction. For Zr, see: (a) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. For Ti, see: (b) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. Catalytic reaction. For Rh, see: (c) Abudulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103. For Pd, see: (d) Dieck, T. H.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243. For Ni, see: (e) Mori, N.; Ikeda, S.; Odashima, K. J. Chem. Soc., Chem. Commun. 2001, 181. Monoyne with allenes, see: (f) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233. Monoyne with allyl tosylates, see: (g) Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 2, 655. Monoyne with enones, see: (h) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 2722.
    • (2000) Org. Lett. , vol.2 , pp. 655
    • Tsukada, N.1    Sugawara, S.2    Inoue, Y.3
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    • 0033620361 scopus 로고    scopus 로고
    • Stoichiometric reaction. For Zr, see: (a) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672. For Ti, see: (b) Suzuki, D.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 2001, 123, 7925. Catalytic reaction. For Rh, see: (c) Abudulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103. For Pd, see: (d) Dieck, T. H.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243. For Ni, see: (e) Mori, N.; Ikeda, S.; Odashima, K. J. Chem. Soc., Chem. Commun. 2001, 181. Monoyne with allenes, see: (f) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233. Monoyne with allyl tosylates, see: (g) Tsukada, N.; Sugawara, S.; Inoue, Y. Org. Lett. 2000, 2, 655. Monoyne with enones, see: (h) Mori, N.; Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1999, 121, 2722.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2722
    • Mori, N.1    Ikeda, S.2    Sato, Y.3
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    • note
    • 2 (13.4 mg, 0.02 mmol) and dppe (15.9 mg, 0.04 mmol) was added 1-hexyne (0.099 g, 1.2 mmol) via a syringe. Dimethyl acetylenedicarboxylate (0.284 g, 2 mmol) was then added to the solution by a syringe. The reaction mixture was stirred under reflux for 1 h. The progress of the reaction was monitored by GLC. After dimethyl acetylenedicarboxylate was consumed, toluene was evaporated in vacuo. Column chromatography of the residue gave 3a as a colorless oil (n-hexane/AcOEt = 80/20, 0.359 g, yield 98%) and 4a as a colorless oil (n-hexane/AcOEt = 60/40, 0.003 g, yield 2%).


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