Anhydrous Solvents for Coupling Reactions

Coupling Reactions

Due to the sensitivity to air and moisture, coupling reactions often require relatively low air and water conditions to initiate the reaction. Therefore, the use of anhydrous solvents is highly recommended to ensure the reaction can be carried out successfully without exposure to high water content from solvents.

Negishi Coupling

Negishi Coupling, a well-known reaction for the preparation of unsymmetrical biaryls. Since organozincs are highly moisture- and air-sensitive, it is critical to set the reaction under water- and air-free conditions. Sigma-Aldrich brand anhydrous solvents are the first choice for such highly water-sensitive reactions.

Negishi coupling

 

Cat no. Product description Greener alternative
227056 N,N-Dimethylformamide, anhydrous, 99.8%  
328634 1-Methyl-2-pyrrolidinone anhydrous, 99.5%  
401757 Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free  
244511 Toluene, anhydrous, 99.8%  
675970 Cyclopentyl methyl ether, contains 50 ppm BHT as inhibitor, anhydrous, ≥99.9% Greener Alternatives
414247 2-Methyltetrahydrofuran, anhydrous, ≥99.0%, contains 250 ppm BHT as stabilizer Greener Alternatives

Suzuki–Miyaura Coupling

One of the more common and moisture-sensitive reactions for C –C bond formations. A cross-coupling of aryl boronic acid with halide in the presence of a palladium catalyst in a relatively dry condition.

Suzuki–Miyaura coupling

 

Cat no. Product description Green alternative
296309 1,4-Dioxane, anhydrous, 99.8%  
401765 Benzene, anhydrous, 99.8%  
401757 Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free  
244511 Toluene, anhydrous, 99.8%  
675970 Cyclopentyl methyl ether, contains 50 ppm BHT as inhibitor, anhydrous, ≥99.9% Greener Alternatives
414247 2-Methyltetrahydrofuran, anhydrous, ≥99.0%, contains 250 ppm BHT as stabilizer Greener Alternatives