8350
S. K. De, R. A. Gibbs / Tetrahedron Letters 46 (2005) 8345–8350
6. Kaur, G.; Kausik, M.; Trehan, S. Tetrahedron Lett. 1997,
38, 2521.
7. Yasuda, M.; Saito, T.; Ueda, M.; Baba, A. Angew. Chem.,
Int. Ed. 2004, 43, 1414.
8. Kim, S. H.; Shin, C.; Pai, A. N.; Koh, H. K.; Chang,
M. H.; Chung, B. Y.; Cho, Y. S. Synthesis 2004,
1581.
9. For recent reports of transition-metal-catalyzed C–C
bond formation through direct hydroxylgroup substitu-
tion with nucleophile other than allylic ones, see: (a)
Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, Y.;
Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124,
10968; (b) Nishibayashi, Y.; Yoshikawa, Y.; Inada, M.;
Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124,
11846.
10. (a) De, S. K. Adv. Synth. Catal. 2005, 347, 673; (b) De,
S. K.; Gibbs, R. A. Tetrahedron Lett. 2005, 46, 1647; (c)
De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2005, 46,
1811; (d) Royer, L.; De, S. K.; Gibbs, R. A. Tetrahedron
Lett. 2005, 46, 4595; (e) De, S. K.; Gibbs, R. A.
Tetrahedron Lett. 2004, 45, 8141; (f) De, S. K. Tetrahedron
Lett. 2004, 45, 2819; (g) De, S. K. Tetrahedron Lett. 2004,
45, 1035.
4.1.12.
1-Allylacenaphthalene
(12). 1H
NMR
(300 MHz, CDCl3) d 7.66–7.61 (m, 2H), 7.52–7.45 (m,
2H), 7.34–7.29 (m, 2H), 5.99–5.85 (m, 1H), 5.20–5.08
(m, 2H), 3.85–3.77 (m, 1H), 3.62–3.53 (m, 1H), 3.17–
3.10 (m, 1H), 2.76–2.66 (m, 1H), 2.51–2.40 (m, 1H);
13C NMR (75 MHz, CDCl3) d 148.7, 144.4, 138.6,
136.5, 131.4, 127.8, 127.7, 122.7, 122.3, 119.2, 118.9,
116.5, 42.6, 40.6, 36.9; EIMS m/z 194 (M+), 153, 77;
HRMS calcd for C15H14 194.1096, found 196.1098.
4.1.13.
1,3-Diphenyl-1-butyne
(13). 1H
NMR
(300 MHz, CDCl3) d 7.45–7.12 (m, 10H), 3.87 (q,
J = 7.2 Hz, 1H), 1.46 (d, J = 7.2 Hz, 3H); 13C NMR
(75 MHz, CDCl3) d 143.2, 131.4, 130.1, 128.5, 128.2,
127.7, 126.8, 123.6, 92.6, 82.5, 32.5, 24.3; EIMS m/z
206 (M+), 191, 189, 77; HRMS calcd for C16H14
206.1096, found 206.1093.
Supplementary data
11. Matano, Y.; Ikegami, T. In Organobismuth Chemistry;
Suzuki, H., Manato, Y., Eds.; Elsevier: New York, 2001;
Chapter 2; pp 21–245.
Supplementary data associated with this article can be
12. (a) De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2004, 45,
7407; For a recent review on the uses of Bi(III) compounds
in organic synthesis, see: (b) Leonard, N. M.; Wieland, L.
C.; Mohan, R. S. Tetrahedron 2002, 58, 8373.
13. The NMR experiment study on a mixed solution of
benzhydrol, allyltrimethylsilane, and a catalytic amount of
BiCl3 in CD2Cl2 at room temperature indicated only the
formation of desired alkene, no other side product was
observed.
References and notes
1. For reviews, see: (a) Sakurai, H. Pure Appl. Chem. 1982,
54, 1; (b) Sakurai, H. Pure Appl. Chem. 1989, 57, 1759.
2. (a) Jung, M. E.; Maderna, A. Tetrahedron Lett. 2004, 45,
5301; for reviews, see: (b) Mukaiyama, T.; Murakami, M.
Synthesis 1987, 1043; (c) Yamamoto, Y.; Asao, N. Chem.
Rev. 1993, 93, 2207.
14. Mostly polymeric product was observed; the similar
observation was reported.4,5
3. Mayor, H.; Gorath, G.; Gand, G.; Bauer, D. Angew.
Chem., Int. Ed. Engl. 1994, 33, 788.
4. Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705.
5. Cella, J. A. J. Org. Chem. 1982, 47, 2125.
15. The reaction was carried out in dichloromethane (2 mL),
alcohol (1 mmol), alkynylsilane (2 mmol), BiCl3 (5 mol%)
at reflux temperature. However, other silyl nucleophiles
such as phenyltrimethylsilane did not work.