A new and efficient synthesis of rosefuran. A general synthesis of furans by palladium-catalysed cycloisomerization of (Z)-2-en-4-yn-1-ols

Chemical Communications

Volumn , Issue 12, 1997, Pages 1083-1084

  Gabriele, Bartolo ^a   Salerno, Giuseppe ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; NATURAL PRODUCT; PALLADIUM; ROSEFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ISOMERISM;

EID: 0030983332     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701988b     Document Type: Article

References (28)

1. K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavour Materials, VCH, Weinheim, 1990.
2. For recent examples, see: A. O. Tucker and M. J. Maciarello, J. Essent. Oil Res., 1995, 7, 653; O. Nishimura, J. Agric. Food Chem., 1995, 43, 2941; D. Karasawa, S. Shatar, A. Erdenechimeg, Y. Okamoto, H. Tateba and S. Shimizu, J. Essent. Oil Res., 1995, 7, 255.
3. For recent examples, see: A. O. Tucker and M. J. Maciarello, J. Essent. Oil Res., 1995, 7, 653; O. Nishimura, J. Agric. Food Chem., 1995, 43, 2941; D. Karasawa, S. Shatar, A. Erdenechimeg, Y. Okamoto, H. Tateba and S. Shimizu, J. Essent. Oil Res., 1995, 7, 255.
4. For recent examples, see: A. O. Tucker and M. J. Maciarello, J. Essent. Oil Res., 1995, 7, 653; O. Nishimura, J. Agric. Food Chem., 1995, 43, 2941; D. Karasawa, S. Shatar, A. Erdenechimeg, Y. Okamoto, H. Tateba and S. Shimizu, J. Essent. Oil Res., 1995, 7, 255.
5. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 4467.
6. C. Lambert, K. Utimoto and H. Nozaki, Tetrahedron Lett., 1984, 25, 5323.
7. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
8. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
9. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
10. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
11. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
12. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
13. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
14. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
15. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
16. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
17. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
18. Reported syntheses of rosefuran from furan derivatives: G. Buchi, E. Sz. Kovats, P. Enggist and G. Uhde, J. Org. Chem., 1968, 33, 1227; O. P. Vig, A. K. Vig, V. K. Handa and S. D. Sharma, J. Indian Chem. Soc., 1974, 51, 900; A. J. Birch, J. Slobbe, Tetrahedron Lett., 1976, 2079; A. Takeda, K. Shinhama and S. Tsuboi, Bull. Chem. Soc. Jpn., 1977, 50, 1903; N. D. Ly and M. Schlosser, Helv. Chim. Acta, 1977, 60, 2085; D. R. Gedge and G. Pattenden, Tetrahedron Lett., 1977, 4443; Z. M. Ismail and H. M. R. Hoffmann, Angew. Chem., 1983, 95, 737; S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1983, 56, 1446; L. Meior and H. D. Scharf, Liebigs Ann. Chem., 1986, 731; W. S. Leal, Y. Kuwahara, T. Suzuki and H. Nakao, Agric. Biol. Chem., 1989, 53, 3279; S. Araki, S.-J. Jin and Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1995, 549; P. Weyerstahl, A. Schenk and H. Marschall, Liebigs Ann. Chem., 1995, 1849.
19. Reported syntheses of rosefuran from nonfuranoid substrates: (a) R. Okazaki, Y. Negishi and N. Inamoto, J. Org. Chem., 1984, 49, 3819; (b) S. Takano, M. Murimoto, S. Satoh and K. Ogasawara, Chem. Lett., 1984, 1261; (c) H. Tsukasa, Agric Biol. Chem., 1989, 53, 3091; (d) R. Iriye, T. Uno, I. Ohwa and A. Konishi, Agric. Biol. Chem., 1990, 54, 1841; (c) J. A. Marshall and W. J. DuBay, J. Org. Chem., 1993, 58, 3602; (f) B. M. Trost and J. A. Flygare, J. Org. Chem., 1994, 59, 1078; (g) A. Barco, S. Benetti, C. De Risi, G. P. Pollini and V. Zanirato, Tetrahedron, 1995, 51, 7721.
20. Reported syntheses of rosefuran from nonfuranoid substrates: (a) R. Okazaki, Y. Negishi and N. Inamoto, J. Org. Chem., 1984, 49, 3819; (b) S. Takano, M. Murimoto, S. Satoh and K. Ogasawara, Chem. Lett., 1984, 1261; (c) H. Tsukasa, Agric Biol. Chem., 1989, 53, 3091; (d) R. Iriye, T. Uno, I. Ohwa and A. Konishi, Agric. Biol. Chem., 1990, 54, 1841; (c) J. A. Marshall and W. J. DuBay, J. Org. Chem., 1993, 58, 3602; (f) B. M. Trost and J. A. Flygare, J. Org. Chem., 1994, 59, 1078; (g) A. Barco, S. Benetti, C. De Risi, G. P. Pollini and V. Zanirato, Tetrahedron, 1995, 51, 7721.
21. Reported syntheses of rosefuran from nonfuranoid substrates: (a) R. Okazaki, Y. Negishi and N. Inamoto, J. Org. Chem., 1984, 49, 3819; (b) S. Takano, M. Murimoto, S. Satoh and K. Ogasawara, Chem. Lett., 1984, 1261; (c) H. Tsukasa, Agric Biol. Chem., 1989, 53, 3091; (d) R. Iriye, T. Uno, I. Ohwa and A. Konishi, Agric. Biol. Chem., 1990, 54, 1841; (c) J. A. Marshall and W. J. DuBay, J. Org. Chem., 1993, 58, 3602; (f) B. M. Trost and J. A. Flygare, J. Org. Chem., 1994, 59, 1078; (g) A. Barco, S. Benetti, C. De Risi, G. P. Pollini and V. Zanirato, Tetrahedron, 1995, 51, 7721.
22. Reported syntheses of rosefuran from nonfuranoid substrates: (a) R. Okazaki, Y. Negishi and N. Inamoto, J. Org. Chem., 1984, 49, 3819; (b) S. Takano, M. Murimoto, S. Satoh and K. Ogasawara, Chem. Lett., 1984, 1261; (c) H. Tsukasa, Agric Biol. Chem., 1989, 53, 3091; (d) R. Iriye, T. Uno, I. Ohwa and A. Konishi, Agric. Biol. Chem., 1990, 54, 1841; (c) J. A. Marshall and W. J. DuBay, J. Org. Chem., 1993, 58, 3602; (f) B. M. Trost and J. A. Flygare, J. Org. Chem., 1994, 59, 1078; (g) A. Barco, S. Benetti, C. De Risi, G. P. Pollini and V. Zanirato, Tetrahedron, 1995, 51, 7721.
23. Reported syntheses of rosefuran from nonfuranoid substrates: (a) R. Okazaki, Y. Negishi and N. Inamoto, J. Org. Chem., 1984, 49, 3819; (b) S. Takano, M. Murimoto, S. Satoh and K. Ogasawara, Chem. Lett., 1984, 1261; (c) H. Tsukasa, Agric Biol. Chem., 1989, 53, 3091; (d) R. Iriye, T. Uno, I. Ohwa and A. Konishi, Agric. Biol. Chem., 1990, 54, 1841; (c) J. A. Marshall and W. J. DuBay, J. Org. Chem., 1993, 58, 3602; (f) B. M. Trost and J. A. Flygare, J. Org. Chem., 1994, 59, 1078; (g) A. Barco, S. Benetti, C. De Risi, G. P. Pollini and V. Zanirato, Tetrahedron, 1995, 51, 7721.
24. Reported syntheses of rosefuran from nonfuranoid substrates: (a) R. Okazaki, Y. Negishi and N. Inamoto, J. Org. Chem., 1984, 49, 3819; (b) S. Takano, M. Murimoto, S. Satoh and K. Ogasawara, Chem. Lett., 1984, 1261; (c) H. Tsukasa, Agric Biol. Chem., 1989, 53, 3091; (d) R. Iriye, T. Uno, I. Ohwa and A. Konishi, Agric. Biol. Chem., 1990, 54, 1841; (c) J. A. Marshall and W. J. DuBay, J. Org. Chem., 1993, 58, 3602; (f) B. M. Trost and J. A. Flygare, J. Org. Chem., 1994, 59, 1078; (g) A. Barco, S. Benetti, C. De Risi, G. P. Pollini and V. Zanirato, Tetrahedron, 1995, 51, 7721.
25. Reported syntheses of rosefuran from nonfuranoid substrates: (a) R. Okazaki, Y. Negishi and N. Inamoto, J. Org. Chem., 1984, 49, 3819; (b) S. Takano, M. Murimoto, S. Satoh and K. Ogasawara, Chem. Lett., 1984, 1261; (c) H. Tsukasa, Agric Biol. Chem., 1989, 53, 3091; (d) R. Iriye, T. Uno, I. Ohwa and A. Konishi, Agric. Biol. Chem., 1990, 54, 1841; (c) J. A. Marshall and W. J. DuBay, J. Org. Chem., 1993, 58, 3602; (f) B. M. Trost and J. A. Flygare, J. Org. Chem., 1994, 59, 1078; (g) A. Barco, S. Benetti, C. De Risi, G. P. Pollini and V. Zanirato, Tetrahedron, 1995, 51, 7721.
26. (a) B. Seiller, C. Bruneau and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1994, 493;
27. (b) B. Seiller, C. Bruneau and P. H. Dixneuf, Tetrahedron, 1995, 51, 13089;
28. (c) H. Kucukbay, B. Cetinkaya, S. Guesmi and P. H. Dixneuf, Organometallics, 1996, 15, 2434.