Ruthenium-catalysed hydrogenation of alkynylstannanes with migration of the stannyl group

Journal of the American Chemical Society

Volumn 126, Issue 42, 2004, Pages 13614-13615

  Shirakawa, Eiji ^a   Morita, Ryotaro ^b   Tsuchimoto, Teruhisa ^b   Kawakami, Yusuke ^b  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; DIMETHYL SULFOXIDE; HYDROGEN; RUTHENIUM COMPLEX; TIN;

ARTICLE; BIOLISTIC TRANSFORMATION; CATALYSIS; CATALYST; ENERGY YIELD; HYDROGENATION; HYDROLYSIS; ISOMERISM; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 6444220131     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0458827     Document Type: Article

References (38)

1. (a) Kosugi, M.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301-302.
2. For recent reviews, see: (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (c) Fugami, K.; Kosugi, M. Top. Curr. Chem. 2002, 219, 87-130.
3. For recent reviews, see: (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (c) Fugami, K.; Kosugi, M. Top. Curr. Chem. 2002, 219, 87-130.
4. trans-Alk-1-en-1-ylstannanes can be obtained by transmetalation between the corresponding alkenylmetals with trialkyltin halides or by hydrostannylation of terminal alkynes: (a) Davies, A. G. Organotin Chemistry, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 8.1.1, pp 114-116 and references therein. For cis-alkenylstannanes through hydrozirconation of alkynylstannanes followed by hydrolysis, see: (b) Lipshutz, B. H.; Keil, R.; Barton, J. C. Tetrahedron Lett. 1992, 33, 5861-5864. For transition-metal-catalyzed carbostannylation of acetylene, see; (c) Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976. (d) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222. (e) Yoshida, H.; Shirakawa, E.; Kurahashi, T.; Nakao, Y.; Hiyama, T. Organometallics 2000, 19, 5671-5678.
5. trans-Alk-1-en-1-ylstannanes can be obtained by transmetalation between the corresponding alkenylmetals with trialkyltin halides or by hydrostannylation of terminal alkynes: (a) Davies, A. G. Organotin Chemistry, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 8.1.1, pp 114-116 and references therein. For cis-alkenylstannanes through hydrozirconation of alkynylstannanes followed by hydrolysis, see: (b) Lipshutz, B. H.; Keil, R.; Barton, J. C. Tetrahedron Lett. 1992, 33, 5861-5864. For transition-metal-catalyzed carbostannylation of acetylene, see; (c) Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976. (d) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222. (e) Yoshida, H.; Shirakawa, E.; Kurahashi, T.; Nakao, Y.; Hiyama, T. Organometallics 2000, 19, 5671-5678.
6. trans-Alk-1-en-1-ylstannanes can be obtained by transmetalation between the corresponding alkenylmetals with trialkyltin halides or by hydrostannylation of terminal alkynes: (a) Davies, A. G. Organotin Chemistry, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 8.1.1, pp 114-116 and references therein. For cis-alkenylstannanes through hydrozirconation of alkynylstannanes followed by hydrolysis, see: (b) Lipshutz, B. H.; Keil, R.; Barton, J. C. Tetrahedron Lett. 1992, 33, 5861-5864. For transition-metal-catalyzed carbostannylation of acetylene, see; (c) Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976. (d) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222. (e) Yoshida, H.; Shirakawa, E.; Kurahashi, T.; Nakao, Y.; Hiyama, T. Organometallics 2000, 19, 5671-5678.
7. trans-Alk-1-en-1-ylstannanes can be obtained by transmetalation between the corresponding alkenylmetals with trialkyltin halides or by hydrostannylation of terminal alkynes: (a) Davies, A. G. Organotin Chemistry, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 8.1.1, pp 114-116 and references therein. For cis-alkenylstannanes through hydrozirconation of alkynylstannanes followed by hydrolysis, see: (b) Lipshutz, B. H.; Keil, R.; Barton, J. C. Tetrahedron Lett. 1992, 33, 5861-5864. For transition-metal-catalyzed carbostannylation of acetylene, see; (c) Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976. (d) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222. (e) Yoshida, H.; Shirakawa, E.; Kurahashi, T.; Nakao, Y.; Hiyama, T. Organometallics 2000, 19, 5671-5678.
8. trans-Alk-1-en-1-ylstannanes can be obtained by transmetalation between the corresponding alkenylmetals with trialkyltin halides or by hydrostannylation of terminal alkynes: (a) Davies, A. G. Organotin Chemistry, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 8.1.1, pp 114-116 and references therein. For cis-alkenylstannanes through hydrozirconation of alkynylstannanes followed by hydrolysis, see: (b) Lipshutz, B. H.; Keil, R.; Barton, J. C. Tetrahedron Lett. 1992, 33, 5861-5864. For transition-metal-catalyzed carbostannylation of acetylene, see; (c) Shirakawa, E.; Yoshida, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975-2976. (d) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221-10222. (e) Yoshida, H.; Shirakawa, E.; Kurahashi, T.; Nakao, Y.; Hiyama, T. Organometallics 2000, 19, 5671-5678.
9. For the addition of Sn-Cu bonds, see: (a) Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934-935. (b) Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. (c) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938. (d) Barbero, A.; Cuadrado, P.; Fleming, I.; González, M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351-352. For Sn-Si bonds, see: (e) Ritter, K. Synthesis 1989, 218-221. For Sn-Al bonds, see: (f) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073. For Sn-Mg bonds, see: (g) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K.; Nozaki, H. J. Organomet. Chem. 1985, 285, 163-172. For Sn-Sn bonds, see: (h) Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
10. For the addition of Sn-Cu bonds, see: (a) Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934-935. (b) Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. (c) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938. (d) Barbero, A.; Cuadrado, P.; Fleming, I.; González, M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351-352. For Sn-Si bonds, see: (e) Ritter, K. Synthesis 1989, 218-221. For Sn-Al bonds, see: (f) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073. For Sn-Mg bonds, see: (g) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K.; Nozaki, H. J. Organomet. Chem. 1985, 285, 163-172. For Sn-Sn bonds, see: (h) Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
11. For the addition of Sn-Cu bonds, see: (a) Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934-935. (b) Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. (c) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938. (d) Barbero, A.; Cuadrado, P.; Fleming, I.; González, M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351-352. For Sn-Si bonds, see: (e) Ritter, K. Synthesis 1989, 218-221. For Sn-Al bonds, see: (f) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073. For Sn-Mg bonds, see: (g) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K.; Nozaki, H. J. Organomet. Chem. 1985, 285, 163-172. For Sn-Sn bonds, see: (h) Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
12. For the addition of Sn-Cu bonds, see: (a) Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934-935. (b) Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. (c) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938. (d) Barbero, A.; Cuadrado, P.; Fleming, I.; González, M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351-352. For Sn-Si bonds, see: (e) Ritter, K. Synthesis 1989, 218-221. For Sn-Al bonds, see: (f) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073. For Sn-Mg bonds, see: (g) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K.; Nozaki, H. J. Organomet. Chem. 1985, 285, 163-172. For Sn-Sn bonds, see: (h) Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
13. For the addition of Sn-Cu bonds, see: (a) Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934-935. (b) Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. (c) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938. (d) Barbero, A.; Cuadrado, P.; Fleming, I.; González, M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351-352. For Sn-Si bonds, see: (e) Ritter, K. Synthesis 1989, 218-221. For Sn-Al bonds, see: (f) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073. For Sn-Mg bonds, see: (g) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K.; Nozaki, H. J. Organomet. Chem. 1985, 285, 163-172. For Sn-Sn bonds, see: (h) Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
14. For the addition of Sn-Cu bonds, see: (a) Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934-935. (b) Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. (c) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938. (d) Barbero, A.; Cuadrado, P.; Fleming, I.; González, M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351-352. For Sn-Si bonds, see: (e) Ritter, K. Synthesis 1989, 218-221. For Sn-Al bonds, see: (f) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073. For Sn-Mg bonds, see: (g) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K.; Nozaki, H. J. Organomet. Chem. 1985, 285, 163-172. For Sn-Sn bonds, see: (h) Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
15. For the addition of Sn-Cu bonds, see: (a) Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934-935. (b) Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. (c) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938. (d) Barbero, A.; Cuadrado, P.; Fleming, I.; González, M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351-352. For Sn-Si bonds, see: (e) Ritter, K. Synthesis 1989, 218-221. For Sn-Al bonds, see: (f) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073. For Sn-Mg bonds, see: (g) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K.; Nozaki, H. J. Organomet. Chem. 1985, 285, 163-172. For Sn-Sn bonds, see: (h) Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
16. For the addition of Sn-Cu bonds, see: (a) Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934-935. (b) Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165-168. (c) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933-4938. (d) Barbero, A.; Cuadrado, P.; Fleming, I.; González, M.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351-352. For Sn-Si bonds, see: (e) Ritter, K. Synthesis 1989, 218-221. For Sn-Al bonds, see: (f) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1989, 54, 5064-5073. For Sn-Mg bonds, see: (g) Matsubara, S.; Hibino, J.; Morizawa, Y.; Oshima, K.; Nozaki, H. J. Organomet. Chem. 1985, 285, 163-172. For Sn-Sn bonds, see: (h) Mitchell, T. N.; Kwetkat, K.; Rutschow, D.; Schneider, U. Tetrahedron 1989, 45, 969-978.
17. For other methods for the synthesis of α-substituted vinylstannanes, see: (a) Verlhac, J.-B.; Kwon, H.; Pereyre, M. J. Chem. Soc., Perkin Trans. 1 1993, 1367-1368. (b) Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R. Tetrahedron 1994, 50, 4853-4872. (c) Shirakawa, E.; Nakao, Y.; Hiyama, T. Chem. Commun. 2001, 263-264. (d) Shirakawa, E.; Nakao, Y.; Tsuchimoto, T.; Hiyama, T. Chem. Commun. 2002, 1962-1963.
18. For other methods for the synthesis of α-substituted vinylstannanes, see: (a) Verlhac, J.-B.; Kwon, H.; Pereyre, M. J. Chem. Soc., Perkin Trans. 1 1993, 1367-1368. (b) Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R. Tetrahedron 1994, 50, 4853-4872. (c) Shirakawa, E.; Nakao, Y.; Hiyama, T. Chem. Commun. 2001, 263-264. (d) Shirakawa, E.; Nakao, Y.; Tsuchimoto, T.; Hiyama, T. Chem. Commun. 2002, 1962-1963.
19. For other methods for the synthesis of α-substituted vinylstannanes, see: (a) Verlhac, J.-B.; Kwon, H.; Pereyre, M. J. Chem. Soc., Perkin Trans. 1 1993, 1367-1368. (b) Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R. Tetrahedron 1994, 50, 4853-4872. (c) Shirakawa, E.; Nakao, Y.; Hiyama, T. Chem. Commun. 2001, 263-264. (d) Shirakawa, E.; Nakao, Y.; Tsuchimoto, T.; Hiyama, T. Chem. Commun. 2002, 1962-1963.
20. For other methods for the synthesis of α-substituted vinylstannanes, see: (a) Verlhac, J.-B.; Kwon, H.; Pereyre, M. J. Chem. Soc., Perkin Trans. 1 1993, 1367-1368. (b) Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R. Tetrahedron 1994, 50, 4853-4872. (c) Shirakawa, E.; Nakao, Y.; Hiyama, T. Chem. Commun. 2001, 263-264. (d) Shirakawa, E.; Nakao, Y.; Tsuchimoto, T.; Hiyama, T. Chem. Commun. 2002, 1962-1963.
21. Although the reaction of trialkyltin chlorides with á-substituted vinylmetals, derived from the corresponding alkenyl halides, must be one of the most straightforward ways to α-substituted vinylstannanes, examples of easily available 2-halo-1-alkene are limited.
22. 4, see: (a) Mitsudo, T.; Nakagawa, Y.; Watanabe, K.; Hori, Y.; Misawa, H.; Watanabe, H.; Watanabe, Y. J. Org. Chem. 1985, 50, 565-571. For the introduction of CO, see: (b) Harris, R. O.; Hota, N. K.; Sadavoy, L.; Yuen, J. M. C. J. Organomet. Chem. 1973, 54, 259-264. For details, see the Supporting Information.
23. 4, see: (a) Mitsudo, T.; Nakagawa, Y.; Watanabe, K.; Hori, Y.; Misawa, H.; Watanabe, H.; Watanabe, Y. J. Org. Chem. 1985, 50, 565-571. For the introduction of CO, see: (b) Harris, R. O.; Hota, N. K.; Sadavoy, L.; Yuen, J. M. C. J. Organomet. Chem. 1973, 54, 259-264. For details, see the Supporting Information.
24. 3 catalyst preheated in DMSO under a nitrogen atmosphere at 80°C for 24 h did not afford 2a at all after 8 h, but did so in 73% yield after 30 h.
25. 3 predominated after 2 h.
26. 12.
27. Although a 1,2-dideuterated product (∼5% yield estimated by GC) was generated in the deuteration of phenylethynylstannane 1i, 2′i can be easily obtained in a pure form through GPC chromatography.
28. Han, X.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600-7605.
29. Verlhac, J.-B.; Pereyre, M. J. Organomet. Chem. 1990, 391, 283-288.
30. 2 moiety when the corresponding carbonyl compounds are available. However, the Wittig reaction sometimes causes the loss and/or scrambling of deuterium atoms. For example, see: (a) Hasselmann, D. Chem. Ber. 1974, 107, 3486-3493. (b) Duñach, E.; Halterman, R. L.; Vollhardt, P. C. J. Am. Chem. Soc. 1985, 107, 1664-1671. (c) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869-9882.
31. 2 moiety when the corresponding carbonyl compounds are available. However, the Wittig reaction sometimes causes the loss and/or scrambling of deuterium atoms. For example, see: (a) Hasselmann, D. Chem. Ber. 1974, 107, 3486-3493. (b) Duñach, E.; Halterman, R. L.; Vollhardt, P. C. J. Am. Chem. Soc. 1985, 107, 1664-1671. (c) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869-9882.
32. 2 moiety when the corresponding carbonyl compounds are available. However, the Wittig reaction sometimes causes the loss and/or scrambling of deuterium atoms. For example, see: (a) Hasselmann, D. Chem. Ber. 1974, 107, 3486-3493. (b) Duñach, E.; Halterman, R. L.; Vollhardt, P. C. J. Am. Chem. Soc. 1985, 107, 1664-1671. (c) Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869-9882.
33. For example, see: (a) Wakatsuki, Y.; Koga, N.; Yamazaki, H.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 8105-8111. See also ref 15b,c. Ruthenium-vinylidene complexes are known to be the key intermediates of the addition reactions to terminal alkynes. For reviews, see: (b) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599-2660. (c) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
34. For example, see: (a) Wakatsuki, Y.; Koga, N.; Yamazaki, H.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 8105-8111. See also ref 15b,c. Ruthenium-vinylidene complexes are known to be the key intermediates of the addition reactions to terminal alkynes. For reviews, see: (b) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599-2660. (c) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
35. For example, see: (a) Wakatsuki, Y.; Koga, N.; Yamazaki, H.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 8105-8111. See also ref 15b,c. Ruthenium-vinylidene complexes are known to be the key intermediates of the addition reactions to terminal alkynes. For reviews, see: (b) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599-2660. (c) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
36. (a) Onitsuka, K.; Katayama, H.; Sonogashira, K.; Ozawa, F. J. Chem. Soc., Chem. Commun. 1995, 2267-2268.
37. (b) Katayama, H.; Ozawa, F. Organometallics 1998, 17, 5190-5196.
38. (c) Katayama, H.; Wada, C.; Taniguchi, K.; Ozawa, F. Organometallics 2002, 21, 3285-3291.