Benzyl thiocyanate

CAS 3012-37-1, Cat. No EN300-127576

Reagent for Pd-catalyzed Cross-coupling cyanation

Benzyl thiocyanate is a reagent solution to a problem of cyanation of aryl nitriles. It is a shelf-stable solid, with a low melting point of 39-41 ℃ and good solubility in diethyl ether, and dioxane. In summary, this reagent is a convenient source for cyanide in a cyanation of boronic acids that is copper(I)-mediated coupling with palladium as a catalyst. Using this protocol, a variety of nitriles can be easily synthesized in high yields: sterically congested substrates, electron-deficient aryl boronic acids, and heteroaryl boronic acids with ease undergo reaction and give good yield.

Synonyms: (Thiocyanatomethyl)benzene; α-Thiocyanatotoluene; Tropeolin

Selected publication

1. 1-Cyanoimidazole as a Mild and Efficient Electrophilic Cyanating Agent.

Wu Y.; Limburg D. C.; Wilkinson D. E.; Hamilton G. S. Org Lett 2000, 2 (6), 795–797. DOI: 10.1021/ol0055263

2. Palladium-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids and Benzylthiocyanate. A Cyanide-Free Cyanation of Boronic Acids.

Zhang Z.; Liebeskind L. S. Org Lett 2006, 8 (19), 4331–4333. DOI: 10.1021/ol061741t