Sonogashira Coupling

Schematic representation of the Sonogashira Coupling.
Mechanism of the Sonogashira Coupling
Mechanism of the Sonogashira Coupling
Sample reactions
intermediate structure intermediate structure
CuI, n-PrNH2, Pd(PPh3)4
PhH
16 °C, 4 h, 76%
intermediate structure
intermediate structure
CuI, Pd(PPh3)2Cl2, Trimethylsilylacetylene
Et3N
RT, 60 min, 98%
intermediate structure
intermediate structure
CuI, Et3N, Pd(PPh3)4, VinylBr
PhMe
RT, 4.5 h, 41%
intermediate structure
intermediate structure
CuI, Et2NH, Pd(PPh3)2Cl2, Trimethylsilylacetylene
PhH
RT, 38 h, 86%
intermediate structure
intermediate structure intermediate structure
CuI, Et2NH, Pd(PPh3)2Cl2
PhH
RT, 40 h, 57%
intermediate structure
intermediate structure
CuI, Et2NH, Pd(PPh3)2Cl2, VinylBr
PhH
RT, 16 h, 70%
intermediate structure
intermediate structure intermediate structure
CuI, Pd(PPh3)2Cl2
Et2NH
RT, 16 h, 94%
intermediate structure