Friedel-Crafts β-Silylvinylations **

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 12, 1997, Pages 1313-1315

  Yamaguchi, Masahiko ^a   Kido, Yoshiyuki ^a   Hayashi, Akio ^a   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Friedel crafts reactions; Gallium; Silicon

Indexed keywords

EID: 0030848347     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199713131     Document Type: Article

References (21)

1. R. Anschütz, Ann. Chem. 1886, 235, 150, 299; O. W. Cook, V. J. Chambers, J. Am. Chem. Soc. 1921, 43, 334; J. S. Reichert, J. A. Nieuwland, ibid. 1923, 45, 3090; J. A. Reilly, J. A. Nieuwland, ibid. 1928, 50, 2564; I. P. Tsukervanik, K. Y. Yuldashev, J. Gen. Chem. USSR 1961, 31, 790.
2. R. Anschütz, Ann. Chem. 1886, 235, 150, 299; O. W. Cook, V. J. Chambers, J. Am. Chem. Soc. 1921, 43, 334; J. S. Reichert, J. A. Nieuwland, ibid. 1923, 45, 3090; J. A. Reilly, J. A. Nieuwland, ibid. 1928, 50, 2564; I. P. Tsukervanik, K. Y. Yuldashev, J. Gen. Chem. USSR 1961, 31, 790.
3. R. Anschütz, Ann. Chem. 1886, 235, 150, 299; O. W. Cook, V. J. Chambers, J. Am. Chem. Soc. 1921, 43, 334; J. S. Reichert, J. A. Nieuwland, ibid. 1923, 45, 3090; J. A. Reilly, J. A. Nieuwland, ibid. 1928, 50, 2564; I. P. Tsukervanik, K. Y. Yuldashev, J. Gen. Chem. USSR 1961, 31, 790.
4. R. Anschütz, Ann. Chem. 1886, 235, 150, 299; O. W. Cook, V. J. Chambers, J. Am. Chem. Soc. 1921, 43, 334; J. S. Reichert, J. A. Nieuwland, ibid. 1923, 45, 3090; J. A. Reilly, J. A. Nieuwland, ibid. 1928, 50, 2564; I. P. Tsukervanik, K. Y. Yuldashev, J. Gen. Chem. USSR 1961, 31, 790.
5. R. Anschütz, Ann. Chem. 1886, 235, 150, 299; O. W. Cook, V. J. Chambers, J. Am. Chem. Soc. 1921, 43, 334; J. S. Reichert, J. A. Nieuwland, ibid. 1923, 45, 3090; J. A. Reilly, J. A. Nieuwland, ibid. 1928, 50, 2564; I. P. Tsukervanik, K. Y. Yuldashev, J. Gen. Chem. USSR 1961, 31, 790.
6. I. P. Tsukervanik, K. Y. Yuldashev, J. Gen. Chem. USSR 1963, 33, 3429; A. G. Martínez, R. M. Alvarez, A. G. Fraile, M. Hanack, L. R. Subramanian, Chem. Ber. 1987, 120, 1255.
7. I. P. Tsukervanik, K. Y. Yuldashev, J. Gen. Chem. USSR 1963, 33, 3429; A. G. Martínez, R. M. Alvarez, A. G. Fraile, M. Hanack, L. R. Subramanian, Chem. Ber. 1987, 120, 1255.
8. We recently reported the direct vinylation reaction of phenols: M. Yamaguchi, A. Hayashi, M. Hirama, J. Am. Chem. Soc. 1995, 117, 1151.
9. See for example: C. C. Price, Org. React. 1946, 3, 1; E. Berliner, ibid. 1949, 5, 229; J. B. Kim, C. Chen, J. K. Krieger, K. R. Judd, C. C. Simpson, E. Berliner, J. Am. Chem. Soc. 1970, 92, 910.
10. See for example: C. C. Price, Org. React. 1946, 3, 1; E. Berliner, ibid. 1949, 5, 229; J. B. Kim, C. Chen, J. K. Krieger, K. R. Judd, C. C. Simpson, E. Berliner, J. Am. Chem. Soc. 1970, 92, 910.
11. See for example: C. C. Price, Org. React. 1946, 3, 1; E. Berliner, ibid. 1949, 5, 229; J. B. Kim, C. Chen, J. K. Krieger, K. R. Judd, C. C. Simpson, E. Berliner, J. Am. Chem. Soc. 1970, 92, 910.
12. G. Stork, E. Colvin, J. Am. Chem. Soc. 1971, 93, 2080.
13. 3 has been used in some Friedel-Crafts alkylations: F. P. Dehaan, H. C. Brown, J. Am. Chem. Soc. 1969, 91, 4844; F. P. Dehaan, H. C. Brown, J. C. Hill, ibid. 1969, 91, 4850.
14. 3 has been used in some Friedel-Crafts alkylations: F. P. Dehaan, H. C. Brown, J. Am. Chem. Soc. 1969, 91, 4844; F. P. Dehaan, H. C. Brown, J. C. Hill, ibid. 1969, 91, 4850.
15. See for example: "Activating and directive effects of silicon": A. R. Bassindale, P. G. Taylor in The Chemistry of Organic Silicon Compounds (Eds.: S. Patai, Z. Rappoport), 1989, Wiley, chapter 14, p. 893.
16. H.-U. Siehl, F.-P. Kaufmann, Y. Apeloig, V. Braude, D. Danovich, A. Berndt, N. Stamatis, Angew. Chem. 1991, 103, 1546; Angew. Chem. Int. Ed. Engl. 1991, 30, 1479; G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, G. A. Olah, J. Am. Chem. Soc. 1992, 114, 3076; C. Dallaire, M. A. Brook, Organometallics 1993, 12, 2332; V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 1996, 188, 3838, and references therein.
17. H.-U. Siehl, F.-P. Kaufmann, Y. Apeloig, V. Braude, D. Danovich, A. Berndt, N. Stamatis, Angew. Chem. 1991, 103, 1546; Angew. Chem. Int. Ed. Engl. 1991, 30, 1479; G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, G. A. Olah, J. Am. Chem. Soc. 1992, 114, 3076; C. Dallaire, M. A. Brook, Organometallics 1993, 12, 2332; V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 1996, 188, 3838, and references therein.
18. H.-U. Siehl, F.-P. Kaufmann, Y. Apeloig, V. Braude, D. Danovich, A. Berndt, N. Stamatis, Angew. Chem. 1991, 103, 1546; Angew. Chem. Int. Ed. Engl. 1991, 30, 1479; G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, G. A. Olah, J. Am. Chem. Soc. 1992, 114, 3076; C. Dallaire, M. A. Brook, Organometallics 1993, 12, 2332; V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 1996, 188, 3838, and references therein.
19. H.-U. Siehl, F.-P. Kaufmann, Y. Apeloig, V. Braude, D. Danovich, A. Berndt, N. Stamatis, Angew. Chem. 1991, 103, 1546; Angew. Chem. Int. Ed. Engl. 1991, 30, 1479; G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, G. A. Olah, J. Am. Chem. Soc. 1992, 114, 3076; C. Dallaire, M. A. Brook, Organometallics 1993, 12, 2332; V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 1996, 188, 3838, and references therein.
20. H.-U. Siehl, F.-P. Kaufmann, Y. Apeloig, V. Braude, D. Danovich, A. Berndt, N. Stamatis, Angew. Chem. 1991, 103, 1546; Angew. Chem. Int. Ed. Engl. 1991, 30, 1479; G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, G. A. Olah, J. Am. Chem. Soc. 1992, 114, 3076; C. Dallaire, M. A. Brook, Organometallics 1993, 12, 2332; V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 1996, 188, 3838, and references therein.
21. J. J. Eisch, J. Am. Chem. Soc. 1962, 84, 3830.