8532
A. Tudose et al. / Tetrahedron Letters 47 (2006) 8529–8533
Table 2. Experimental data for the Suzuki–Miyaura reaction of p-bromoanisole with trans-2-phenylvinylboronic acid, catalysed by systems 8a and
9a in the presence of various basesa
Base
8a
Conversionb (trans:cis)c (%)
9a
Conversionb (%) (trans:cis)c
2 h
8 h
24 h
48 h
2 h
8 h
24 h
48 h
Li2CO3
Na2CO3
K2CO3
Cs2CO3
KF
24 (18:82)
31 (32:68)
52 (84:16)
69 (99:1)
37 (23:77)
46 (27:73)
54 (32:68)
70 (40:60)
91 (76:24)
21 (16:84)
26 (34:66)
51 (84:16)
54 (99:1)
34 (20:80)
65 (37:63)
79 (78:22)
83 (96:4)
41 (25:75)
78 (37:63)
88 (75:25)
97 (89:11)
95 (82:18)
47 (30:70)
82 (39:61)
91 (74:26)
57 (36:64)
78 (77:23)
95 (95:5)
66 (39:61)
88 (77:23)
100 (88:12)
88 (88:12)
100 (86:14)
69 (87:13)
92 (83:17)
a Experimental conditions: Pd(OAc)2, 0.01 mmol; imidazolium salt, 0.04 mmol; base, 4 mmol; trans-2-phenylvinylboronic acid, 2.4 mmol; 1,4-
dioxane, 2 mL; 1 mL of a solution containing 2 mmol of p-bromoanisole and n-decane in dioxane; 80 °C, under nitrogen.
b Based on p-bromoanisole and determined by GC using decane as an internal standard.
c Trans:cis stereoselectivity of 4-methoxystilbene determined by GC.
M. K.; Weskamp, T.; Herrmann, W. A. J. Organomet.
Chem. 2000, 595, 186–190; (d) Gsto¨ttmayr, C. W. K.;
Bo¨hm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann,
W. A. Angew. Chem., Int. Ed. 2002, 41, 1363–1365; (e)
Navarro, O.; Kelly, R. A., III; Nolan, S. P. J. Am. Chem.
Soc. 2003, 125, 16194–16195; (f) Schneider, S. K.; Herr-
mann, W. A.; Herdtweck, E. J. Mol. Catal. A: Chem.
2005, 245, 248–254.
also found serendipitly that the inorganic base markedly
affects the trans/cis stereochemistry of the target
compound.
Acknowledgements
The authors acknowledge the ‘Fonds National de la
Recherche Scientifique’ (FNRS), Brussels, for the
purchase of major instrumentations. A.T. benefited of
a fellowship granted from the ‘Belgian Science Policy
Office’ in order to promote the S&T cooperation with
Central and Eastern Europe.
5. (a) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J.
Org. Chem. 1999, 64, 3804–3805; (b) Zhang, C.; Trudell,
M. L. Tetrahedron Lett. 2000, 41, 595–598; (c) Furstner,
¨
A.; Leitner, A. Synlett 2001, 290–292; (d) Grasa, G. A.;
Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan,
S. P. Organometallics 2002, 21, 2866–2873; (e) Altenhoff,
G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew.
Chem., Int. Ed. 2003, 42, 3690–3693; (f) Altenhoff, G.;
Goddard, R.; Lehmann, C. W.; Glorius, F. J. Am. Chem.
Soc. 2004, 126, 15195–15201.
Supplementary data
6. (a) Kuhn, N.; Kratz, T. Synthesis 1993, 561–562; (b)
Hahn, F. E.; Wittenbecher, L.; Boese, R.; Bla¨ser, D.
Chem. Eur. J. 1999, 5, 1931–1935.
Supplementary data associated with this article can be
7. (a) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles,
J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem.,
Int. Ed. Engl. 1995, 34, 1021–1023; (b) Teles, J. H.;
Melder, J.-P.; Ebel, K.; Schneider, R.; Gehrer, E.; Harder,
W.; Brode, S.; Enders, D.; Breuer, K.; Raabe, G. Helv.
Chim. Acta 1996, 79, 61–83; (c) Scholl, M.; Ding, S.; Lee,
C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953–956.
8. Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T.
E.; Scholl, M.; Choi, T.-L.; Ding, S.; Day, M. W.; Grubbs,
R. H. J. Am. Chem. Soc. 2003, 125, 2546–2558.
References and notes
1. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508–
524; (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org.
React. 1997, 50, 1–652.
2. For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev.
1995, 95, 2457–2483; (b) Suzuki, A. J. Organomet. Chem.
1999, 576, 147–168; (c) Miyaura, N. Top. Curr. Chem.
2002, 219, 11–59; (d) Kotha, S.; Lahiri, K.; Kashinath, D.
Tetrahedron 2002, 58, 9395–9633; (e) Suzuki, A. J.
Organomet. Chem. 2002, 653, 83–90; (f) Bellina, F.;
Carpita, A.; Rossi, R. Synthesis 2004, 2419–2440; (g)
Suzuki, A. Chem. Commun. 2005, 4759–4763; (h) Tudose,
A.; Maj, A.; Sauvage, X.; Delaude, L.; Demonceau, A.;
Noels, A. F. In Education in Advanced Chemistry; Marci-
niec, B., Ed.; Organic and Polymer Synthesis and Cata-
lysis; Wydawnictwo Poznanskie: Poznan–Wroclaw, 2006;
Vol. 10, p 155.
9. (a) Nyce, G. W.; Csihony, S.; Waymouth, R. M.; Hedrick,
J. L. Chem. Eur. J. 2004, 10, 4073–4079; (b) Bedford, R.
B.; Betham, M.; Blake, M. E.; Frost, R. M.; Horton, P.
´
´
N.; Hursthouse, M. B.; Lopez-Nicolas, R.-M. Dalton
Trans. 2005, 2774–2779; (c) Bedford, R. B.; Betham, M.;
Bruce, D. W.; Danopoulos, A. A.; Frost, R. M.; Hird, M.
J. Org. Chem. 2006, 71, 1104–1110.
10. Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R.
Tetrahedron 1999, 55, 14523–14534.
11. (a) Delaude, L.; Szypa, M.; Demonceau, A.; Noels, A. F.
Adv. Synth. Catal. 2002, 344, 749–756; (b) Delaude, L.;
Demonceau, A.; Noels, A. F. Curr. Org. Chem. 2006, 10,
203–215; (c) Aidouni, A.; Demonceau, A.; Delaude, L.
Synlett 2006, 493–495; (d) Tudose, A.; Demonceau, A.;
3. (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc.
2000, 122, 4020–4028; (b) Barder, T. E.; Walker, S. D.;
Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005,
127, 4685–4696; (c) Anderson, K. W.; Buchwald, S. L.
Angew. Chem., Int. Ed. 2005, 44, 6173–6177.
12. (a) Scho¨ssler, W.; Regitz, M. Chem. Ber. 1974, 107, 1931–
1948; (b) Kuhn, N.; Steimann, M.; Weyers, G. Z.
Naturforsch. 1999, 54b, 427–433; (c) Ishiguro, K.; Hira-
bayashi, K.; Nojima, T.; Sawaki, Y. Chem. Lett. 2002,
4. (a) Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J.
Organomet. Chem. 1998, 557, 93–96; (b) Weskamp, T.;
Bo¨hm, V. P. W.; Herrmann, W. A. J. Organomet. Chem.
1999, 585, 348–352; (c) Bo¨hm, V. P. W.; Gsto¨ttmayr, C.