A range of silver iminoalkyl imidazol-2-ylidene complexes have been isolated in good yield
(50%–85%) and characterised by
Metal carbene complexes have been widely employed to catalyse Heck reactions, cross-coupling (such as Suzuki-Miyaura coupling) [
The single crystal X-ray diffraction data were recorded on a Nonius CCD Kappa diffractometer (graphite-monochromated Mo K
Silver oxide (I) (0.45 g, 1.93 mmol) was added to a solution of imidazolium salt (
Complexes
White solid; yield: 0.21 g, 50%; 1H NMR (DMSO-d6, 400 MHz)
White solid; yield: 0.47 g, 84%; mp 85.5–
White solid; yield: 0.25 g, 68%; 1H NMR (DMSO-d6, 400 MHz)
White solid; yield: 0.34 g, 78%; 1H NMR (DMSO-d6, 400 MHz)
White solid; yield: 0.16 g, 66%; 1H NMR (DMSO-d6, 400 MHz)
White solid 0.11 g, 91%; mp 85.0–
White solid; yield: 0.071 g, 60%; mp 68.2–
White solid (0.27 g, 85%); 1H NMR (CDCl3, 400 MHz)
White solid (0.064 g, 77%); 1H NMR (CD2Cl2, 400 MHz)
The synthesis of iminoalkyl imidazolium salts
Synthesis of benzylhydrylideneaminoalkyl imidazol-2-ylidene silver complexes
R1 | R2 | Product yield | |
---|---|---|---|
H | Bn | ||
Bn | Bn | ||
Me | Bn | ||
Bn | |||
H | Ph | ||
Bn | Ph | ||
Me | Ph | ||
Ph |
Synthesis of benzylhydrylideneaminoalkyl imidazol-2-ylidene silver complexes
The silver carbene transfer agent (
Synthesis of benzylideneaminoalkyl imidazol-2-ylidene
The deprotonation of imidazolium salts
The deprotonation of
Crystal data and structure refinement.
Empirical formula | C25 H23 Ag Br N3 | |
Formula weight | 553.24 | |
Temperature | 173(2) K | |
Wavelength | 0.71073 Å | |
Crystal system | Triclinic | |
Space group | P | |
Unit cell dimensions | a = 8.1675(2) Å | |
b = 8.6875(3) Å | ||
c = 16.5972(6) Å | ||
Volume | 1123.49(6) Å3 | |
Z | 2 | |
Density (calculated) | 1.64 Mg/m3 | |
Absorption coefficient | 2.69 mm−1 | |
F(000) | 552 | |
Crystal size | 0.25 | |
Theta range for data collection | 3.89 to 25.03°. | |
Index ranges | −9 | |
Reflections collected | 16098 | |
Independent reflections | 3930 [R(int) = 0.043] | |
Reflections with I | 3495 | |
Completeness to theta = 25.03° | 98.9% | |
Refinement method | Full-matrix least-squares on F2 | |
Data/restraints/parameters | 3930/0/363 | |
Goodness-of-fit on F2 | 1.071 | |
Final R indices [I | R1 = 0.027, wR2 = 0.063 | |
R indices (all data) | R1 = 0.033, wR2 = 0.066 | |
Largest diff. peak and hole | 0.42 and −0.53 |
Selected bond distances and angles for
Angles | Distances (Å) | ||
C(1)-Ag-Br | 154.76(8) | Ag-C(1) | 2.015(3) |
C(1)-Ag- | 109.20(7) | Ag-Br | 2.4969(3) |
Br-Ag- | 95.823(11) | Ag- | 3.0549(4) |
Ag-Br- | 84.177(11) | N(1)-C(1) | 1.353(4) |
C(1)-N(1)-C(2) | 111.1(2) | N(1)-C(2) | 1.382(4) |
C(1)-N(1)-C(4) | 124.7(2) | N(1)-C(4) | 1.460(4) |
C(2)-N(1)-C(4) | 124.0(3) | N(2)-C(1) | 1.350(4) |
C(1)-N(2)-C(3) | 111.0(2) | N(2)-C(3) | 1.392(4) |
C(1)-N(2)-C(11) | 125.1(2) | N(2)-C(11) | 1.462(4) |
N(2)-C(1)-Ag | 129.5(2) | N(3)-C(13) | 1.278(4) |
N(1)-C(1)-Ag | 126.19(19) |
X-ray crystal structure of silver carbene complex
X-ray crystal structure of
X-ray crystallographic data of
A range of silver iminoalkyl imidazole-2-ylidene complexes have been synthesised and characterised. The single crystal X-ray diffraction study of