Stille Coupling

Schematic representation of the Stille Coupling.

Mechanism of the Stille Coupling

Mechanism of the Stille Coupling

Original publication	J. Am. Chem. Soc.. 1978, 100, 3636. J. Am. Chem. Soc.. 2007, 129, 1890.
Reviews	Angew. Chem. Int. Ed.. 1986, 25, 508. J. Chem. Soc., Perkin Trans. 1. 1999, 1, 1235. J. Organomet. Chem.. 1986, 304, 1. Org. React.. 1997, 50, 1. Pure Appl. Chem.. 1996, 68, 73. Synthesis. 1992, 0, 803.

Sample reactions

intermediate structure

(Me3Sn)2, LiCl, Pd(PPh3)4

THF

60 °C, , 80%

intermediate structure

intermediate structure

intermediate structure

CO, LiCl, Pd2(dba)3, Ph3As

3.5 atm

NMP

70 °C, , 80%

intermediate structure

intermediate structure

CuCl, Pd(PPh3)4, CuCl2

DMSO

60 °C, 2 h, 82%

intermediate structure

intermediate structure

LiCl, Pd(PPh3)4

THF

RT, 7 d

intermediate structure

intermediate structure

n-Bu3SnH, Pd(PPh3)4

THF

RT, 60 min, 86%

intermediate structure

intermediate structure

Pd(PPh3)4, VinylSnBu3

Dioxane

100 °C, 16 h, 91%

intermediate structure

intermediate structure

intermediate structure

CuCl, LiCl, Pd(PPh3)4

DMSO

RT, 10 min, 53% (3 steps)

intermediate structure

intermediate structure

intermediate structure

CuCl, LiCl, Pd(PPh3)4

DMSO

60 °C, 60 min, 61% (3 steps)

intermediate structure

intermediate structure

n-Bu3SnH, Pd(PPh3)4

PhMe

RT, 20 min, 88%

intermediate structure

intermediate structure

intermediate structure

i-Pr2NEt, Pd2(dba)3

NMP

RT, 22 h, 62%

intermediate structure

intermediate structure

Pd(PPh3)4, (n-Bu3Sn)2

PhMe

110 °C, 24 h, 70%

intermediate structure

intermediate structure

intermediate structure

CuI, Pd2(dba)3.CHCl3, Ph3As

DMF

RT, 48 h, 100%

intermediate structure

intermediate structure

intermediate structure

PdCl2.2MeCN

DMF

RT, ON, 68%

intermediate structure

intermediate structure

intermediate structure

Pd(PPh3)2Cl2

DMF

90 °C, 5 h, 74%

intermediate structure

intermediate structure

Pd2(dba)3, Ph3As, CuBr.Me2S

DMSO, THF

RT, 1 h, 78%

intermediate structure

intermediate structure

LiCl, Pd2(dba)3, VinylSnBu3, (2-Furyl)3P

NMP

RT, 1 h, 69%

intermediate structure

intermediate structure

intermediate structure

Pd2(dba)3

CH2Cl2

RT, 3 h, 60%

intermediate structure