Categories: C-S Bond Formation >
Synthesis of thiocyanates
Recent Literature
A practical, rapid, and efficient microwave (MW) promoted nucleophilic
substitution of alkyl halides or tosylates with alkali adzides, thiocyanates
or sulfinates in aqueous media tolerates various reactive functional groups.
Y. Ju, D. Kumar, R. S. Varma, J. Org. Chem., 2006, 71, 6697-6700.
A novel and highly selective method uses triphenylphosphine,
diethylazodicarboxylate and NH4SCN for the conversion of
alcohols, thiols, carboxylic acids, silyl ethers, and silyl carboxylates to
their corresponding thiocyanates.
N. Iranpoor, H. Firouzabadi, B. Akhlaghinia, R. Azadi, Synthesis, 2004,
92-96.
A mild oxidation of selected anions (N3-, SCN-, I-, and Br-) by ceric ammonium
nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides β-functionalized
ketones in short reaction times. This method provides an alternative
pathway to important starting materials and intermediates in organic synthesis.
J. Jiao, L. X. Nguyen, D. R. Patterson, R. A. Flowers II, Org. Lett., 2007,
9, 1323-1326.
Anhydrous FeCl3 oxidizes potassium thiocyanate to the corresponding
radical and promotes subsequent addition to nucleophilic olefins to produce
dithiocyanate derivatives under mild conditions with excellent yields and
chemoselectivities. The use of ferric chloride makes this method simple,
convenient and practical.
J. S. Yadav, B. V. S. Reddy, M. K. Gupta, Synthesis,
2004, 1983-1986.
