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CAS 3012-37-1, Cat. No EN300-127576
Reagent for Pd-catalyzed сross-coupling cyanation

Benzyl thiocyanate

Benzyl thiocyanate is a reagent solution to the cyanation problem of aryl nitriles1. It is a shelf-stable solid, with a low melting point (39-41 ℃) and good solubility in diethyl ether, and dioxane2. This reagent is a convenient source for cyanide in a cyanation of boronic acids that is copper(I)-mediated coupling with palladium as a catalyst2. Using this protocol, a variety of nitriles can be easily synthesized: sterically congested substrates, electron-deficient aryl boronic acids, and heteroaryl boronic acids with ease undergo reaction and give good yield2.

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

Selected publication

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

    Wu Y.; Limburg D.; Wilkinson D.; Hamilton G. 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. Org Lett 2006, 8 (19), 4331–4333. DOI: 10.1021/ol061741t

 

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