96
W.A. Herrmann et al. / Journal of Organometallic Chemistry 557 (1998) 93–96
Crystal data, data collection and refinement parame-
ters are presented in Table 2.
vigorously and heated to the appropriate reaction tem-
perature. 0.5 ml-samples were removed after every hour
and sealed in GC-vials for the gas chromatographic
determination of the yield. The work-up was achieved
by filtering of the hot reaction mixture and subsequent
cooling of the organic phase. The product was obtained
by either crystallization (after several hours at room
temperature) or by evaporation of the triethylamine.
Crystallographic data (excluding structure factors)
for the structures reported in this paper have been
deposited with the Cambridge Crystallographic Data
Centre. Copies of the data can be obtained free of
charge on application to the Director, CCDC, 12
Union Road, Cambridge CB2 1EZ, UK (fax: +44
(1223) 336-033, e-mail: teched@chemcrys.cam.ac.uk).
4.3. Suzuki procedure
Acknowledgements
In a 30 ml pressure tube was placed the aryl halide
(10 mmol), arylboronic acid (11 mmol), potassium car-
bonate (20 mmol) with 1 mol% catalyst and 10 ml
toluene. The reaction mixture was vigorously stirred
and heated to 120°C for 12–48 h. Subsequently the
cooled reaction mixture was extracted twice with water
and the organic phase was separated. The solvent was
removed under vacuum and the crude product was
purified by chromatography on a silica gel or by
recrystallization.
This work was supported by the German Science
Foundation (DFG). We would like to thank Dr K.
8
Ofele and Dr J. Fischer for stimulating discussions.
References
[1] Review: W.A. Herrmanm, C. Ko¨cher, Angew. Chem. 1997, in
press.
[2] (a) W.A. Herrmann, M. Elison, J. Fischer, C. Ko¨cher, G.R.J.
Artus, Angew. Chem. 107 (1995) 2602; Angew. Chem. Int. Ed.
Engl. 34 (1995) 2371. (b) W.A. Herrmann, L.J. Gooßen, C.
Ko¨cher, G.R.J. Artus, Angew. Chem. 108 (1996) 2980; Angew.
Chem. Int. Ed. Engl. 35 (1996) XXXX.
4.4. Heck procedure
[3] W.A. Herrmann, L.J. Gooßen, M. Spiegler, J. Organomet.
Chem. 1997, in press.
In a 50 ml three-necked flask equipped with a septum
inlet, a thermometer and a reflux condenser (Hg-bub-
bler) were placed aryl halide (25 mmol), anhydrous
sodium acetate (2.25 g, 23 mmol), diethyleneglycol di-n-
butylether (0.5 g, GC standard) and N,N-dimethyl-
acetamide (20 ml). The reaction mixture was degassed
under vacuum and argon was passed over the con-
denser for 5 min to ensure an inert reaction atmo-
sphere. N-butyl acrylate (5 ml, 35 mmol) was then
added last because of possible loss by evaporation. The
reaction mixture was vigorously stirred and heated to
the appropriate reaction temperature. After thermostat-
ing for 10 min, a preheated catalyst solution (67 mg
catalyst in 10 ml solvent, 0.5 mol% Pd) was injected by
syringe (start, t=0). Work-up was achieved by pouring
the reaction mixture at room temperature into an ex-
cess of water, extracting with dichloromethane or di-
ethyl ether, and drying with magnesium sulphate. After
removal of the extraction solvent and N,N-dimethylac-
etamide, the products were purified by distillation or
recrystallisation.
8
[4] (a) W.A. Herrmann, C. Broßmer, K. Ofele, C.-P. Reisinger, T.
Priermeier, M. Beller, H. Fischer, Angew. Chem. Int. Ed. Engl.
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8
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107 (1995) 1992; Angew. Chem. Int. Ed. Engl. 34 (1995) 1848. (c)
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Organometallic Compounds, VCH, Weinheim, 1996, pp. 712-
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8
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4.5. Alkyne coupling procedure
[11] W.A. Herrmann, M. Gardiner, C.-P. Reisinger, manuscript in
preparation.
[12] STOE&CIE. GMBH, IPDS Operating System Version 2.6. 1995,
Darmstadt, Deutschland.
[13] A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, J.
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Deutschland.
In a 100 ml three-necked flask equipped with a
septum inlet, a thermometer and a reflux condenser
were placed aryl bromide (10 mmol), phenylacetylene
(12 mmol), 54 mg (1 mol% Pd) catalyst, diethylenegly-
col-di-n-butylether (0.2 g, GC standard), and triethy-
lamine (30 ml). The reaction mixture was stirred
.