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),
achieved
q
via
(quartet),
DEPT90
m
and
(multiplet).
DEPT135
13C
spectra.
assignment
MS
spectra
was
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
Arylhalides
with
1
(GP
1)
–
Sonogashira
coupling
N,N-Bistrimethylsilylpropargylamine
of
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;
1H
NMR
(Frequenz MHz, solvent): δ = x (Multiplizität, J = x.x Hz,
x H), 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
Reaktionszeit
were
converted
reaction
according
time,
to
purification
GP
2.
by
After
column
chromatography (PE:EA:Et2NH, x:x:x) afforded x mg (x µmol, x%)
of product Praktikant Nr, as a Farbe/ Feststoff Flüssigkeit.
~
MP.: x°C; Rf (PE:EA, x:x) = x; IR (neat):  = x cm-1, x;
1H
NMR
(Frequenz MHz, solvent): δ = x (Multiplizität, J = x.x Hz,
x H), x;
13C
NMR (Frequenz MHz, solvent): x (Multiplizität), ,;
Masse: wird hier beim abtippen der Daten näher erklärt: