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Synthesis of isothiocyanates
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A ZnI2-catalyzed addition of ammonium thiocyanate to olefins in the presence
of 4-toluenesulfonic acid and tetrabutylammonium iodide proceeds by a Markovnikov-type process and a radical
isomerization to provide the corresponding isothiocyanates selectively and in good yields.
N. Taniguchi, Synlett, 2023,
34, 73-76.
An electrochemical benzylic isothiocyanation provides isothiocyanate
derivatives in a highly chemo- and site-selective manner under external
oxidant-free conditions. The method exhibits high functional group compatibility
and is suitable for late-stage functionalization of bioactive molecules.
S. Zhang, Y. Li, T. Wang, M. Li, L. Wen, W. Gup, Org. Lett.,
2022, 24, 1742-1746.
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.