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Synthesis 2001(10): 1551-1555
DOI: 10.1055/s-2001-16082
DOI: 10.1055/s-2001-16082
PAPER
© Georg Thieme Verlag Stuttgart · New York
Studies on Pyrazines; 38: [1] Acylation of Bromopyrazines and 2-Bromopyridine via Copper-Cocatalytic Stille Reaction
Weitere Informationen
Received
28 February 2001
Publikationsdatum:
23. September 2004 (online)
Publikationsverlauf
Publikationsdatum:
23. September 2004 (online)
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Abstract
Synthesis of acetylpyrazines 3 and propionylpyrazines 5 was achieved by copper-cocatalytic Stille reaction of bromopyrazines 1 with tributyl(1-ethoxyalkenyl)tin and then acidic hydrolysis. The optimal reaction conditions involve the combination of 15 mol% CuI with 5 mol% of PdCl2(Ph3P)2. Similarly, 2-acylpyridines and propionylbenzenes were prepared from the corresponding aryl bromides.
Key words
cross-coupling - copper(I) iodide - organotin compounds - pyrazinyl ketones - acylpyridines
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References
The Cu-cocatalytic coupling of 1a was hardly impeded in the presence of 1 equivalent of acetophenone, which provided a 90 % yield of 5a.