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Synthesis of isothiocyanates
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A facile and general protocol for the preparation of isothiocyanates from
alkyl and aryl amines relies on a tosyl chloride mediated decomposition of a
dithiocarbamate salts that are generated in situ by treatment of amines with
carbon disulfide and triethylamine. Vairous alkyl- and arylisothiocyanates have
been prepared in good yield.
R. Wong, S. J. Dolman, J. Org. Chem., 2007,
72, 3969-3971.
A photocatalyzed, efficient, and mild reaction of amines with carbon disulfide
provides aliphatic and aromatic
isothiocyanates in good yields, which are significant organic building blocks and biological
diagnostic markers.
J. Ma, F. Li, C. Wang, Z. Wang, C. Du, L. Wang, Org. Lett., 2023, 25,
5692-5696.
A practical, mild, high-yielding, and supporting-electrolyte-free
electrochemical method enables the preparation of aliphatic and aromatic
isothiocyanates from amine and carbon disulfide without using toxic and
expensive reagents.
C. Kiaku, J. M. Walsh, M. C. Leech, D. L. Poole, J. Mason, J. C. A. Goodall,
P. Devo, K. Lam, Org. Lett., 2023, 25,
1147-1150.
In the presence of trifluoromethanesulfonyl chloride, triphenylphosphine, and
sodium iodide, a broad range of thiocarbamyl fluorides and isothiocyanates can
be synthesized from secondary and primary amines in good yields, respectively.
The reactions offer good functional group compatibility.
J. Wei, S. Liang, L. Jiang, W. Yi, J. Org. Chem., 2020, 85,
12374-12381.
A two-step, one-pot reaction of primary amines or their salts with carbon
disulfide, followed by reaction of the intermediate dithiocarbamates with T3P
provides isothiocyanates in good yields. T3P® (propane phosphonic acid anhydride)
acts as an efficient desulfurating agent.
Ł Janczewski, A. Gajda, S. Frankowski, T. M. Goszczyński, T. Gajda, Synthesis, 2018, 50,
1141-1151.
Reactions of thiocarbonyl fluoride derived from CF3SiMe3, elemental sulfur, and KF with secondary amines
provides a wide variety of thiocarbamoyl
fluorides in good yields at room temperature in THF, whereas the reaction with primary
amines gives isothiocyanates. The
two reactions show broad substrate scope and good functional group tolerance.
Moreover, AgSCF3 can be used as an alternative.
L. Zhen, H. Fan, X. Wang, L. Jiang,
Org. Lett., 2019, 21, 2106-2110.
A facile and efficient synthesis of isothiocyanates involves the reaction of
amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide
by either a one-pot process or a two-step approach. The one-pot process is
useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the
two-step approach is more versatile.
Z.-Y. Li, H.-Z. Ma, C. Han, H.-T. Xi, Q. Meng, X. Chen, X.-Q. Sun, Synthesis, 2013, 45,
1667-1674.