2778
S. Ma, Q. He / Tetrahedron 62 (2006) 2769–2778
(MC, 18.60), 204 (100.00); IR (neat): 1940, 1596,
1491 cmK1. Anal. Calcd for C18H16: C, 93.06; H, 6.94;
found: C, 92.92; H, 7.05.
Chem. Lett. 2000, 1360. (j) Marshall, J. A.; Adams, N. D. J. Org.
Chem. 1999, 64, 5201. (k) Shen, Q.; Hammond, G. B. J. Am.
Chem. Soc. 2002, 124, 6534. For reviews see: (a) Transition
Metal Reagents and Catalysts: Innovations in Organic
Synthesis; Tsuji, J., Ed.; Wiley: Chichester, 2002; Chapter 6.
(b) Comprehensive Carbanion Chemistry Part B: Selectivity in
Carbon–Carbon Bond Forming Reactions; Buncel, E., Durst,
T., Eds.; Elsevier: Amsterdam, 1984; Chapter 3. (c) Ma, S. Eur.
J. Org. Chem. 2004, 1175.
3.2.2.19. Synthesis of 2,2-diphenyl vinylidenecyclo-
hexane (15).
Ph
Ph
3. (a) Ma, S.; Wang, L. J. Org. Chem. 1998, 63, 3497. (b) Ma, S.;
Wang, L. Chin. J. Chem. 1999, 17, 531. (c) Ma, S.; Zhang, A.
J. Org. Chem. 1998, 63, 9601. (d) Ma, S.; Zhang, A.; Yu, Y.;
Xia, W. J. Org. Chem. 2000, 65, 2287. (e) Ma, S.; Zhang, A.
J. Org. Chem. 2002, 67, 2287. (f) Ma, S.; Wang, G. Angew.
Chem., Int. Ed. 2003, 42, 4215.
15
The reaction of 1-cyclohexyl-2-phenylacetylene 9 (94 mg,
0.51 mmol), n-BuLi (0.95 mL, 1.52 mmol, 1.6 M in
hexanes), ZnBr2 (343 mg, 1.52 mmol), Pd(PPh3)4 (29 mg,
5 mol%), and iodobenzene (171 mL, 1.52 mmol) afforded
15 (59 mg, 44%) as a solid, mp 97–98 8C (petroleum ether);
1H NMR (300 MHz, CDCl3) dZ7.40–7.20 (m, 10H), 2.32–
2.28 (m, 4H), 1.73–1.65 (m, 4H), 1.61–1.55 (m, 2H); 13C
NMR (75.4 MHz, CDCl3) dZ200.4, 138.2, 128.4, 128.2,
126.6, 107.4, 105.6, 31.4, 27.6, 26.1; MS (70 eV): m/z (%):
260 (MC, 90.62), 217 (100.00); IR (neat): 1945, 1597,
1488 cmK1. Anal. Calcd for C20H20: C, 92.26; H, 7.74;
found: C, 92.24; H, 7.86.
4. (a) Bauer, D.; Koebrich, G. Chem. Ber. 1976, 109, 2185. (b)
Koebrich, G.; Merkel, D. Justus Liebigs Ann. Chem. 1972,
761, 50. (c) Merkel, D.; Koebrich, G. Chem. Ber. 1973, 106,
¨
2025. (d) Militzer, H.-C.; Schoemenauer, S.; Otte, C.; Puls, C.;
¨
Hain, J.; Brase, S.; Meijere, A. Synthesis 1993, 10, 998. (e)
Maercker, V. A.; Girreser, U. Angew. Chem. 1990, 102, 718.
¨
(f) Meijere, A.; Jaekel, F.; Simon, A.; Borrmann, H.; Koehler,
J.; Johnels, D.; Scott, L. T. J. Am. Chem. Soc. 1991, 113, 3935.
(g) Meijere, A.; Kozhushkov, S.; Puls, C.; Haumann, T.;
Boese, R.; Cooney, M. J.; Scott, L. T. Angew. Chem. 1994,
106, 934. Angew. Chem. Int. Ed. 1994, 33, 869. (h) Meijere,
A.; Kozhushkov, S.; Haumann, T.; Boese, R.; Puls, C.;
Cooney, M. J.; Scott, L. T. Chem. Eur. J. 1995, 1, 124. (i)
Scott, L. T.; Cooney, M. J.; Otte, C.; Puls, C.; Haumann, T.;
Boese, R.; Carroll, P. J.; Smith, A. B.; Meijere, A. J. Am.
Chem. Soc. 1994, 116, 10275. (j) Ingo, E.; Thomas, L.;
Meijere, A. J. Organomet. Chem. 2001, 624, 110. (k) Milic, J.;
Schirmer, H.; Flynn, B. L.; Noltemeyer, M.; Meijere, A.
Synlett 2002, 875.
Acknowledgements
Financial support from the National Natural Science
Foundation of China, the Major State Basic Research
Development Program (Grant No. G2000077500) and
Shanghai Municipal Committee of Science and Technology
are greatly appreciated.
5. For a seminal report of Negishi cross coupling, see: King, A. O.;
Okukado, N.; Negishi, E. J. Chem. Soc., Chem. Commun. 1977,
683. For a review, see: Negishi, E.; Liu, F. In Metal-catalyzed
Cross-couplingReactions;Stang, P.J.;Diederich, F.,Eds.;VCH:
Weinheim, 1998; pp 1–47.
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¨
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