Experimental Section

Experimental Section

General methods: Chemicals (Aldrich, Fluka, Lancaster, and Merck) were used without further purification. Diethyl ether and tetrahydrofuran were dried over sodium. NMR spectra were recorded on Bruker ARX500, ARX300 and AMX250 spectrometers. Chemical shifts were referenced to residual solvent protons. Signal multiplicity as follows: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet). 13C assignment was achieved via DEPT90 and DEPT135 spectra. MS spectra were recorded on a Finnigan MAT 90 a Varian 711 or a micrOTOF-Q spektrometer. IR spectra were recorded on a Bruker Vector 22.

General procedure 1 (GP 1) – Sonogashira coupling of Arylhalides with N,N-Bistrimethylsilylpropargylamine and subsequent preparation of aryl-substituted propargylamides X:

6.02 mmol arylhalide are dissolved in 10 ml triethylamine and the mixture is degassed for three times. After the addition of 70.4 mg (100 µmol) (Ph3P)2PdCl2 the solution is stirred for 10 min and 1.00 g (5.01 mmol) of the alkyne and 9.60 mg (50 µmol) CuI are added. After stirring the solution for 16 hours at the indicated temperature, the resulting dark mixture is filtered over a column filled with basic alumina (PE:EA:Et2NH, 10:1:0.1). After evaporation of the solvent, the products X are used for the next step without further purification.

The resulting amine X, is dissolved in 10 ml dry DCM and 5.01 mmol of acid chloride is added at room temperature. After the addition of 501 µmol TBAF (1 M in THF) the solution is stirred for 16 h. 10 ml aqueous HCl solution (1 M) is added and the phases are separated. The aqueous phase is extracted two times with 25 ml DCM and the combined organic phases are dried over MgSO4, filtered and the residue is absorbed on celite. The crude product is purified by column chromatography on silica.

General procedure 2 (GP 2) – Gold catalyzed conversion of amides X:

The starting amides are dissolved in dry DCM and 5 mol% of the gold catalyst X are added. After stirring for the denoted time at rt, the products are purified by column chromatography on basic alumina (deactivated with 0.1% Et2NH).

Preparation of Verbindungsname Praktikant Nr

Struktur

According to GP 1 1.23 g (6.02 mmol) Name des Arylhalogenids are converted at Temperaturangabe. The resulting raw amine was converted with xx mg (5.01 mmol) Säurechlorid as described in GP 1. x mg (2.20 mmol, x% over 2 steps) product Praktikant Nr were gained after purification by column chromatography (PE:EE, 5:1) as a Farbe/ Feststoff Flüssigkeit.

MP.: x°C; Rf (PE:EA, x:x) = x; IR (neat): = x cm-1, x; 1HNMR (Frequenz MHz, solvent): δ = x (Multiplizität, J = x.x Hz, xH), x; 13C NMR (Frequenz MHz, solvent): x (Multiplizität), ,; Masse: wird hier beim Abtippen der Daten näher erklärt:

Preparation of Verbindungsname Praktikant Nr:

Struktur

x mg (x µmol) amide Praktikant Nr and x mg (x µmol) gold catalyst x were converted according to GP 2. After Reaktionszeit reaction time, purification by column chromatography (PE:EA:Et2NH, x:x:x) afforded x mg (x µmol, x%) of product Praktikant Nr, as a Farbe/ Feststoff Flüssigkeit.