Categories: C-S Bond Formation >
Synthesis of thiocyanates
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A practical, rapid, and efficient microwave (MW) promoted nucleophilic
substitution of alkyl halides or tosylates with alkali azides, 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.
Ionic liquids [bmim][X] (X = Cl, Br, I, OAc, SCN) are highly efficient reagents
for nucleophilic substitution reactions of sulfonate esters derived from primary
and secondary alcohols. The newly developed protocol is very environmentally
attractive because the reactions use stoichiometric amounts of ionic liquids as
sole reagents without additional solvents and activating reagents. Moreover,
these ionic liquids can be readily recycled.
Y. Liu, Y. Xu, S. H. Jung, J. Chae, Synlett, 2012, 23,
2663-2666.
A cross-coupling reaction of arylboronic acids with KSCN salt to yield aryl
thiocyanates is catalyzed by copper acetate in the presence of 4-methylpyridine
serving both as ligand and base under 0.2 MPa of molecular oxygen. Various
arylboronic acids were suitable under the reaction conditions.
N. Sun, H. Zhang, W. Mo, B. Hu, Z. Shen, X. Hu, Synlett, 2013, 24,
1443-1447.
Various aromatic and heteroaromatic compounds have been efficiently thiocyanated
by using a combination of bromodimethylsulfonium bromide (BDMS) and ammonium
thiocyanate.
D. S. Bhalerao, K. G. Agamanchi, Synlett, 2007,
2952-2956.
A stereoselective gold-catalyzed hydrothiocyanation of haloalkynes provided
vinyl thiocyanates in good yields. Furthermore, a sulfur-based gold catalyst
(PPh3AuSCN) has shown a unique reactivity in gold-catalyzed reactions
such as the cyclization of N-propargylic amides.
X. Zeng, B. Chen, Z. Lu, G. B. Hammond, B. Xu,
Org. Lett., 2019, 21, 2772-2776.
A simple and efficient FeCl3-mediated method for the α-thiocyanation
of ketones produces α-oxo thiocyanates in very good yields and with high
selectivity under mild conditions. The use of inexpensive and readily available
iron(III) chloride makes this procedure simple, convenient and practical.
J. S. Yadav, B. V. S. Reddy, U. V. S. Reddy, D. N. Chary, Synthesis, 2008,
1283-1287.
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.