Sonogashira Coupling

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