A. S. K. Hashmi, A. M. Schuster, M. Schmuck, F. Rominger
FULL PAPER
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through a small column of basic alumina and washed twice with
PE/EA/DEA (200 mL, 10:1:0.1). After removal of the solvent in
vacuo, the crude product was used in subsequent reactions without
further purification.
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General Procedure C (GP C). Synthesis of Carboxamides with N,N-
Bis(trimethylsilyl)propargylamines: In a flame-dried Schlenk flask
under a nitrogen atmosphere, N,N-bis(trimethylsilyl)propargyl-
amine (1 equiv.) was dissolved in CH2Cl2. Acid chloride (1.1 equiv.)
and TBAF (10 mol-%) were added. The reaction was stirred at
room temp. overnight. After that the crude product was absorbed
on Celite by concentration of the reaction mixture and Celite 545
in vacuo. The reaction mixture was purified by flash chromatog-
raphy on silica.
General Procedure D (GP D). Gold Catalysis: In a dry Schlenk
flask or a dry sealed vial, the gold catalyst (5 mol-%) and the silver
salt (5 mol-%) were dissolved in the indicated solvent and stirred
for 1 h. N-Propargylcarboxyamide (1 equiv.) was added and the re-
action was stirred at the indicated temperature for the indicated
time. The reaction progress was monitored by TLC or GC/MS
measurements. After that the crude product was absorbed on Celite
by concentration of the reaction mixture and Celite 545 in vacuo.
The reaction mixture was purified by flash chromatography on sil-
ica.
[9] CCDC-808210 (for 2a), -808211 (for 2z), -808212 (for 2ar),
-808213 (for 2as), -808214 (for 2at), -808215 (for 3q) and
-808216 (for 3ar) contain the supplementary crystallographic
data for this paper. These data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
www.ccdc.cam.ac.uk/data_request/cif.
Supporting Information (see footnote on the first page of this arti-
cle): Experimental procedures and characterization data for com-
pounds 1a–1r, 2a–2ay, 3a–4e, 4a–4e, 3h, 3j, 5k, 6m, 6n, 3o–3q, 3t,
7ac, 7ae, 3ae, 7ag, 3ag, 7ak, 3af, 3aj, 3ak, 3an, 7ao, 7aq, 2ar, 2as,
2ak, 7av, 8av, 7aw, 3ax, 3ay, 9q.
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Acknowledgments
This work was supported by the Deutsche Forschungsgemeinschaft
(DFG) (SFB 623) and by Umicore AG & Co. KG.
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Received: March 10, 2011
Published Online: June 22, 2011
4602
www.eurjoc.org
© 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2011, 4595–4602