S. S. Pr o¨ ckl et al. / Tetrahedron 61 (2005) 9855–9859
9859
Filtered samples were extracted with water/CH Cl and
2
dried over MgSO . Products were identified by GC/MS.
4
Baidossi, M.; Sasson, Y. Adv. Synth. Catal. 2002, 344,
348–354.
2
Conversions and yields were quantified by GLC using
diethylene glycol dibutylether as internal standard
3. Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.;
Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127–14136.
4. (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121,
(
D ZG5%).
rel
1
1101–11107. (b) Buchmeiser, M. R.; Schareina, T.; Kempe,
4.2. Typical reaction conditions for Heck reactions with
bromobenzene
R.; Wurst, K. J. Organomet. Chem. 2001, 634, 39–46. (c)
Silberg, J.; Schareina, T.; Kempe, R.; Wurst, K.; Buchmeiser,
M. R. J. Organomet. Chem. 2001, 622, 6–18. (d) Ley, S. V.;
Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.;
McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D.
J. Chem. Soc., Chem. Commun. 2002, 1134–1135.
1
0 mmol bromobenzene, 15 mmol styrene, 12 mmol
NaOAc, about 0.001 mol% Pd/support, 10 mL NMP
1-methyl-2-pyrrolidone), TZ140 8C, 2–4 h.
(
5
. (a) Mehnert, C. P.; Ying, J. Y. J. Chem. Soc., Chem. Commun.
1
997, 2215–2216. (b) Mehnert, C. P.; Weaver, D. W.; Ying, J.
4.3. Typical reaction conditions for Heck reactions with
aryl chlorides
Y. J. Am. Chem. Soc. 1998, 120, 12289–12296. (c) Djakovitch,
L.; K o¨ hler, K. J. Am. Chem. Soc. 2001, 123, 5990–5999. (d)
Srivastava, R.; Venkatathri, N.; Srinivas, D.; Ratnasamy, P.
Tetrahedron Lett. 2003, 44, 3649–3651.
. Pr o¨ ckl, S. S.; Kleist, W.; Gruber, M. A.; K o¨ hler, K. Angew.
Chem., Int. Ed. 2004, 43, 1881–1882.
. Biffis, A.; Zecca, M.; Basato, M. J. Mol. Catal. A: Chem. 2001,
1
0 mmol aryl chloride, 12 mmol styrene, 12 mmol
Ca(OH) , 0.01–0.1 mol% Pd/support, 10 mL NMP, TZ
2
6
7
8
1
60 8C, 2–6 h.
4
.4. Typical reaction procedure for kinetic investigations
1
73, 249–274.
. (a) Kaneda, K.; Higuchi, M.; Imanaka, T. J. Mol. Catal. 1990,
3, L33–L36.(b)LeBlond, C.R.;Andrews,A. T.;Sun, Y.;Sowa,
Sixteen identical experiments were performed in 16
pressure tubes as described above. At defined times the
reactions were quenched. For Pd leaching 5 mL of the
filtered sample were evaporated. Pd content of the residue
was analyzed by flame AAS.
6
J. R. Org. Lett. 2001, 3, 1555–1557. (c) Reetz, M. T.;
Westermann, E. Angew. Chem. 2000, 112, 165–168.
. Shmidt, A. F.; Mametova, L. V. Kinet. Catal. 1996, 37,
9
4
06–408.
0. Zhao, F.; Murakami, K.; Shirai, M.; Arai, M. J. Catal. 2000,
94, 479–483.
1
1
4
.5. Recycling experiments
1
1. (a) K o¨ hler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J.
Chem. Eur. J. 2002, 8, 622–631. (b) Schmidt, A. F.; Smirnov,
V. V. J. Mol. Catal. A: Chem. 2003, 203, 75–78.
1
0
0 mmol bromobenzene, 15 mmol styrene, 12 mmol NaOAc,
.2 mol% Pd/Al O , 10 mL NMP, TZ140 8C, tZ6 h. After
2
3
the reaction was finished, the catalyst was washed three
times with CH Cl and re-used.
1
2. (a) Reetz, M. T.; Westermann, E.; Lohmer, R.; Lohmer, G.
Tetrahedron Lett. 1998, 39, 8449–8452. (b) de Vries, A. H. M.;
Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J.
W.; de Vries, J. G. Org. Lett. 2003, 5, 3285–3288. (c) Reetz,
M. T.; de Vries, J. G. Chem. Commun. 2004, 1559–1563.
3. (a) Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J.; K o¨ hler, K.
J. Mol. Catal. A: Chem. 2002, 182–183, 499–509. (b)
Heidenreich, R. G.; K o¨ hler, K.; Krauter, J. G. E.; Pietsch, J.
Synlett 2002, 7, 1118–1122.
2
2
Acknowledgements
1
1
The authors thank M. Barth and his co-workers for
palladium analyses.
4. (a) Pearlman, W. Tetrahedron Lett. 1967, 17, 1663–1664. (b)
Djakovitch, L.; Heise, H.; K o¨ hler, K. J. Organomet. Chem.
1999, 584, 16–26. (c) Fessi, S.; Ghorbel, A. J. Sol-Gel Sci.
Technol. 2000, 19, 417–420.
References and notes
1
. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100,
009–3066.
. (a) Zhao, F.; Arai, M. React. Kinet. Catal. Lett. 2004, 81,
81–289. (b) Mukhopadhyay, S.; Rothenberg, G.; Joshi, A.;
15. de Vries, A. H. M.; Parlevliet, F. J.; Schmieder-van de
Vondervoort, L.; Mommers, J. H. M.; Henderickx, H. J. W.;
Walet, M. A. M.; de Vries, J. G. Adv. Synth. Catal. 2002, 344,
996–1002.
3
2
2