6526
C. Dupuis et al. / Tetrahedron Letters 42 (2001) 6523–6526
Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829–
3. For coupling reactions of aryl chlorides in organic
6839.
medium, see: Stu¨rmer, R. Angew. Chem., Int. Ed. 1999,
38, 3307–3308; For early examples, see: (a) Old, D. W.;
Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998,
120, 9722–9723; Wolfe, J. P.; Singer, R. A.; Yang, B. H.;
Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550–9561;
(b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc.
2000, 122, 4020–4028; (c) Weskamp, T.; Bohm, V. P. W.;
Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348–
352.
11. Typical procedure: Water and acetonitrile were degassed
under vacuum. Pd(OAc)2 (5 mol%, 0.025 mmol, 5.6 mg),
TPPTS (15%; 0.075 mmol, 128 mg of a 33% wt solution
in water) and 0.16 mL of water were placed in a flask
under argon and warmed at 60°C for 15 min. A solution
of 4-bromobenzaldehyde (1 equiv., 0.5 mmol, 58 mL) and
phenylboronic acid (1.2 equiv., 0.6 mmol, 73 mg) in 0.5
mL of acetonitrile was added in the flask. Diisopropy-
lamine (2.5 equiv., 1.25 mmol, 175 mL) was then added in
the flask and the resulting mixture was stirred 4 h at
80°C. Reaction progress was monitored by GC and when
the reaction was completed, the mixture was quenched
with 5 mL of saturated NaCl solution and extracted by
3×5 mL of ethyl acetate. The organic layers were com-
bined, dried over MgSO4, filtered and concentrated in
vacuo. Purification of crude product by flash chromatog-
raphy on silica gel afforded 77 mg of 4-phenylbenzalde-
hyde (85%) as a solid. F=56°C; 1H NMR (CDCl3, 200
MHz, l ppm): 7.44–7.56 (3H, m); 7.67 (2H, dd); 7.73
(2H, d); 7.98 (2H, d); 10.1 (1H, s, CHO); 13C (CDCl3, 50
MHz, d ppm): 127.3; 127.6; 128.4; 128.9; 130.2; 135.1;
139.6; 147.1; 191.8 (CHO).
4. (a) Darses, S.; Jeffery, T.; Brayer, J.-L.; Demoute, J.-P.;
Geneˆt, J.-P. Tetrahedron Lett. 1996, 37, 3857–3860; (b)
Darses, S.; Jeffery, T.; Brayer, J.-L.; Demoute, J.-P.;
Geneˆt, J.-P. Bull. Soc. Chim. Fr. 1996, 133, 1095–1102; (c)
Darses, S.; Brayer, J.-L.; Demoute, J.-P.; Geneˆt, J.-P.
Tetrahedron Lett. 1997, 38, 4393–4396; (d) Darses, S.;
Michaut, G.; Geneˆt, J.-P. Eur. J. Org. Chem. 1999,
1875–1883.
5. For reviews, see: Geneˆt, J.-P.; Savignac, M. J.
Organomet. Chem. 1999, 576, 305–317; Geneˆt, J.-P.; Sav-
ignac, M.; Lemaire-Audoire, S. In IUPAC Monographs
Chemistry for the 21st Century; Murahashi, S.-I.; Davies,
S. G., Eds. Transition metal catalysed reactions, 1999,
pp. 55 and references cited therein.
12. Bell, L. N.; Burke, M. T.; Hodgson, Jr., G. L.; Shu-
maker, T. K. Eur. Pat. Appl. EP 59, 983 (1982).
13. Koch, K.; Chambers, R. J.; Biggers, M. S. Synlett 1994,
347–348.
6. Galland, J.-C.; Savignac, M.; Geneˆt, J.-P. Tetrahedron
Lett. 1997, 38, 8695–8698.
7. Geneˆt, J.-P.; Lindquist, A.; Blart, E.; Mourie`s, V.; Savig-
nac, M. Tetrahedron Lett. 1995, 36, 1443–1446.
8. (a) Galland, J.-C.; Savignac, M.; Geneˆt, J.-P. Tetrahedron
Lett. 1999, 40, 2323–2326; (b) Galland, J.-C.; Dias, S.;
Savignac, M.; Geneˆt, J.-P. Tetrahedron 2001, to be
published.
8
14. (a) Beller, M.; Fischer, H.; Hermann, A.; Ofele, K.;
Brossmer, C. Angew. Chem., Int. Engl. 1995, 34, 1848–
1849; (b) Albisson, D. A.; Bedford, R. B.; Laurence, S.
E.; Scully, P. N. J. Chem. Soc., Chem. Commun. 1998,
2095–2096; (c) Bedford, R. B.; Welch, S. J. Chem. Soc.,
Chem. Commun. 2001, 129–130.
9. Dupuis, C. Ph.D.; Universite´ Pierre et Marie Curie: Paris,
December 1999.
15. Moreno-Man˜as, M.; Pe´rez, M.; Pleixats, R. J. Org.
10. Amatore, C.; Blart, E.; Geneˆt, J.-P.; Jutand, A.; Lemaire-
Chem. 1996, 61, 2346–2351.