Synthesis of Isothiocyanates and Unsymmetrical Thioureas
with the Bench-Stable Solid Reagent (Me4N)SCF3
Posted on 2017-03-29 - 21:49
A highly efficient,
selective, and rapid transformation of primary
amines and diamines to isothiocyanates and cyclic thioureas is disclosed.
As opposed to established approaches that employ toxic or volatile
electrophilic liquids and require reaction control (i.e., slow addition,
cooling), this protocol utilizes the bench-stable, solid reagent (Me4N)SCF3 at room temperature. The method is characterized
by operational simplicity, high speed, efficiency, high functional
group tolerance, and late-stage applicability. The byproducts are
solids, allowing isolation of the target compounds by filtration.
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Scattolin, Thomas; Klein, Alexander; Schoenebeck, Franziska (2017). Synthesis of Isothiocyanates and Unsymmetrical Thioureas
with the Bench-Stable Solid Reagent (Me4N)SCF3. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b00689
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AUTHORS (3)
TS
Thomas Scattolin
AK
Alexander Klein
FS
Franziska Schoenebeck
KEYWORDS
diamineBench-Stabletarget compoundsspeedIsothiocyanateelectrophilic liquidscoolingisolationReagentroom temperaturelate-stage applicabilityapproachtransformationSynthesisimplicityfiltrationisothiocyanateaminesreaction controlUnsymmetrical Thioureasreagenti.ebench-stablegroup toleranceefficiencymethodsolidbyproductcyclic thioureas