Sonogashira Coupling

Schematic representation of the Sonogashira Coupling.

Mechanism of the Sonogashira Coupling

Mechanism of the Sonogashira Coupling

Original publication	Tetrahedron Lett.. 1975, 16, 4467. J. Org. Chem.. 2009, 74, 7052.
Reviews	Angew. Chem. Int. Ed.. 2007, 46, 834. Chem. Rev.. 2007, 107, 874. Chem. Soc. Rev.. 2011, 40, 5084.

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

intermediate structure

CuI, Et3N, Pd(PPh3)4

DMF

80 °C, 2 d, 78%

intermediate structure