Highly Chemo- and Regioselective Intermolecular Cyclotrimerization of Alkynes Catalyzed by Cationic Rhodium(I)/Modified BINAP Complexes

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4697-4699

  Tanaka, Ken ^a   Shirasaka, Kaori ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE; CYCLOPROPANE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; CYCLOTRIMERIZATION; MOLECULAR DYNAMICS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0346780615     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035963s     Document Type: Article

References (40)

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2. For reviews, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (c) Ojima, I.; Tzamarioudaki, M.; Zhaoyang, L.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 46-92. (e) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374-1382. (f) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 536-556. (h) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770.
3. For reviews, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (c) Ojima, I.; Tzamarioudaki, M.; Zhaoyang, L.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 46-92. (e) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374-1382. (f) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 536-556. (h) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770.
4. For reviews, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (c) Ojima, I.; Tzamarioudaki, M.; Zhaoyang, L.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 46-92. (e) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374-1382. (f) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 536-556. (h) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770.
5. For reviews, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (c) Ojima, I.; Tzamarioudaki, M.; Zhaoyang, L.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 46-92. (e) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374-1382. (f) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 536-556. (h) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770.
6. For reviews, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (c) Ojima, I.; Tzamarioudaki, M.; Zhaoyang, L.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 46-92. (e) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374-1382. (f) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 536-556. (h) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770.
7. For reviews, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (c) Ojima, I.; Tzamarioudaki, M.; Zhaoyang, L.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 46-92. (e) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374-1382. (f) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 536-556. (h) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770.
8. For reviews, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596. (c) Ojima, I.; Tzamarioudaki, M.; Zhaoyang, L.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 46-92. (e) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374-1382. (f) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 536-556. (h) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770.
9. Ni(0)-catalyzed cocyclotrimerization of methyl propiolate and terminal alkynes was reported. Although the regioselectivity is high, chemoselectivity is moderate, and the reaction requires slow addition of methyl propiolate (over 5-60 min) and a substoichiometric amount of zinc(II) phenoxide: Mori, N.; Ikeda, S.-I.; Odashima, K. Chem. Commun. 2001, 181-182.
10. For Ni(0)-catalyzed cocyclotrimerization of alkynes using a large excess of acetylene gas, see: Sato, Y.; Ohashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231-5234.
11. Palladacyclopentadiene-mediated cocyclotrimerization of two molecules of dimethyl acetylenedicarboxylate and one molecule of diphenylacetylene was reported (76% yield), but this reaction proceeded in low yield (40% yield) under catalytic conditions (regioselectivity is not relevant to this case): Dieck, H. T.; Munz, C.; Müller, C. J. Organomet. Chem. 1990, 384, 243-255.
12. Stoichiometric zirconium-and copper-mediated cocyclotrimerization of alkynes, see: Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672-1680.
13. For papers on catalytic intramolecular cyclotrimerization of alkynes, see: (a) Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Chem. Eur. J. 2003, 9, 2469-2483. (b) Jeevanandam, A.; Korivi, R. P.; Huang, I.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810. (c) Sugihara, T.; Wakabayashi, A.; Nagai, Y.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2002, 9, 576-577. (d) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67. (e) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431. (f) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 9, 549-550. (g) Hillard III, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.
14. For papers on catalytic intramolecular cyclotrimerization of alkynes, see: (a) Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Chem. Eur. J. 2003, 9, 2469-2483. (b) Jeevanandam, A.; Korivi, R. P.; Huang, I.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810. (c) Sugihara, T.; Wakabayashi, A.; Nagai, Y.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2002, 9, 576-577. (d) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67. (e) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431. (f) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 9, 549-550. (g) Hillard III, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.
15. For papers on catalytic intramolecular cyclotrimerization of alkynes, see: (a) Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Chem. Eur. J. 2003, 9, 2469-2483. (b) Jeevanandam, A.; Korivi, R. P.; Huang, I.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810. (c) Sugihara, T.; Wakabayashi, A.; Nagai, Y.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2002, 9, 576-577. (d) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67. (e) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431. (f) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 9, 549-550. (g) Hillard III, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.
16. For papers on catalytic intramolecular cyclotrimerization of alkynes, see: (a) Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Chem. Eur. J. 2003, 9, 2469-2483. (b) Jeevanandam, A.; Korivi, R. P.; Huang, I.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810. (c) Sugihara, T.; Wakabayashi, A.; Nagai, Y.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2002, 9, 576-577. (d) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67. (e) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431. (f) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 9, 549-550. (g) Hillard III, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.
17. For papers on catalytic intramolecular cyclotrimerization of alkynes, see: (a) Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Chem. Eur. J. 2003, 9, 2469-2483. (b) Jeevanandam, A.; Korivi, R. P.; Huang, I.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810. (c) Sugihara, T.; Wakabayashi, A.; Nagai, Y.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2002, 9, 576-577. (d) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67. (e) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431. (f) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 9, 549-550. (g) Hillard III, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.
18. For papers on catalytic intramolecular cyclotrimerization of alkynes, see: (a) Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Chem. Eur. J. 2003, 9, 2469-2483. (b) Jeevanandam, A.; Korivi, R. P.; Huang, I.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810. (c) Sugihara, T.; Wakabayashi, A.; Nagai, Y.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2002, 9, 576-577. (d) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67. (e) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431. (f) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 9, 549-550. (g) Hillard III, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.
19. For papers on catalytic intramolecular cyclotrimerization of alkynes, see: (a) Yamamoto, Y.; Nagata, A.; Nagata, H.; Ando, Y.; Arikawa, Y.; Tatsumi, K.; Itoh, K. Chem. Eur. J. 2003, 9, 2469-2483. (b) Jeevanandam, A.; Korivi, R. P.; Huang, I.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810. (c) Sugihara, T.; Wakabayashi, A.; Nagai, Y.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2002, 9, 576-577. (d) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67. (e) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431. (f) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 9, 549-550. (g) Hillard III, R. L.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058-4069.
20. For recent papers on the rhodium-catalyzed intramolecular cyclotrimerization of alkynes, see: (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (b) Nishiyama, H.; Niwa, E.; Inoue, T. ; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574. (c) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859. (d) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748. (e) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (f) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564. (g) McDonald, F. E.; Zhu, H. Y. E.; Homquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
21. For recent papers on the rhodium-catalyzed intramolecular cyclotrimerization of alkynes, see: (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (b) Nishiyama, H.; Niwa, E.; Inoue, T. ; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574. (c) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859. (d) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748. (e) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (f) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564. (g) McDonald, F. E.; Zhu, H. Y. E.; Homquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
22. For recent papers on the rhodium-catalyzed intramolecular cyclotrimerization of alkynes, see: (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (b) Nishiyama, H.; Niwa, E.; Inoue, T. ; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574. (c) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859. (d) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748. (e) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (f) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564. (g) McDonald, F. E.; Zhu, H. Y. E.; Homquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
23. For recent papers on the rhodium-catalyzed intramolecular cyclotrimerization of alkynes, see: (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (b) Nishiyama, H.; Niwa, E.; Inoue, T. ; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574. (c) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859. (d) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748. (e) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (f) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564. (g) McDonald, F. E.; Zhu, H. Y. E.; Homquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
24. For recent papers on the rhodium-catalyzed intramolecular cyclotrimerization of alkynes, see: (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (b) Nishiyama, H.; Niwa, E.; Inoue, T. ; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574. (c) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859. (d) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748. (e) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (f) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564. (g) McDonald, F. E.; Zhu, H. Y. E.; Homquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
25. For recent papers on the rhodium-catalyzed intramolecular cyclotrimerization of alkynes, see: (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (b) Nishiyama, H.; Niwa, E.; Inoue, T. ; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574. (c) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859. (d) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748. (e) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (f) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564. (g) McDonald, F. E.; Zhu, H. Y. E.; Homquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
26. For recent papers on the rhodium-catalyzed intramolecular cyclotrimerization of alkynes, see: (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785. (b) Nishiyama, H.; Niwa, E.; Inoue, T. ; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574. (c) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859. (d) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748. (e) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430. (f) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564. (g) McDonald, F. E.; Zhu, H. Y. E.; Homquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
27. For pioneering work of the rhodium-catalyzed intramolecular cyclotrimerization of alkynes, see: Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1357-1364.
28. (a) Field, L. D.; Ward, A. J.; Turner, P. Aust. J. Chem. 1999, 52, 1085-1092.
29. (b) Ohshita, J.; Furumori, K.; Matsuguchi, A.; Ishikawa, M. J. Org. Chem. 1990, 55, 3277-3280.
30. For rhodium clusters catalyzed intermolecular cyclotrimerization of terminal alkynes, see: Baidossi, W.; Goren, N.; Blum, J. J. Mol. Catal. 1993, 85, 153-162.
31. For recent papers on the cationic rhodium(I) complex-catalyzed reaction of alkynes, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078-8079. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157-159. (c) Tong, X.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 6370-6371. (d) Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339-6343. (e) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772.
32. For recent papers on the cationic rhodium(I) complex-catalyzed reaction of alkynes, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078-8079. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157-159. (c) Tong, X.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 6370-6371. (d) Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339-6343. (e) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772.
33. For recent papers on the cationic rhodium(I) complex-catalyzed reaction of alkynes, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078-8079. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157-159. (c) Tong, X.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 6370-6371. (d) Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339-6343. (e) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772.
34. For recent papers on the cationic rhodium(I) complex-catalyzed reaction of alkynes, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078-8079. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157-159. (c) Tong, X.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 6370-6371. (d) Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339-6343. (e) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772.
35. For recent papers on the cationic rhodium(I) complex-catalyzed reaction of alkynes, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078-8079. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157-159. (c) Tong, X.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 6370-6371. (d) Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339-6343. (e) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772.
36. Saito, T.; Yokozawa, T.; Zhang, X.; Sayo, N. EP 850945A, 1998; US 5872273, 1999.
37. Zhang, X. Mashimo, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron. Lett. 1991, 32, 7283-7286.
38. In this reaction, major byproducts are 1:2 (= 1/4) cocyclotrimerization products.
39. The use of rhodium(I)/DTBM-SEGPHOS complex for the cocyclotrimerization of 1 and 4 significantly lowered the yield of 5 as a result of the generation of 2 and 3 as byproducts. The use of rhodium(I)/Tol-BINAP complex significantly decreased the regioselectivity of 5.
40. For the formation of cyclophanes by cyclotrimerization of bis-terminal diynes with nitriles, see: Moretto, A. F.; Zhang, H.-C; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157-3158.