Trichloroisocyanuric Acid (TCCA)
Recent Literature
An efficient oxidation of primary alcohols to the corresponding aldehydes can be
carried out at room temperature in DCM, using trichloroisocyanuric acid in the
presence of catalytic TEMPO: aliphatic, benzylic, and allylic alcohols, and
β-amino alcohols are rapidly oxidized without no overoxidation to carboxylic
acids. The slow oxidation of secondary carbinols makes the reaction highly
chemoselective.
L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett., 2001,
3, 3041-3043.
In a direct conversion of primary and secondary alcohols into the corresponding
α-chloro aldehydes and α-chloro ketones, trichloroisocyanuric acid serves both
as stoichiometric oxidant and α-halogenating reagent. For primary alcohols,
TEMPO has to be added as an oxidation catalyst, and for the transformation of
secondary alcohols MeOH as an additive is essential to
promote chlorination of the intermediary ketones.
Y. Jing, C. G. Daniliuc, A. Studer, Org. Lett.,
2014,
16, 4932-4935.
The use of trihaloisocyanuric acid/triphenylphosphine enables a regioselective
conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides
under mild and neutral conditions in acetonitrile. The reactions proceed
smoothly in high yield at room temperature and at reflux, respectively, over a
short time.
V. S. C. de Andrade, M. C. S. de Mattos,
Synthesis, 2016, 48, 1381-1388.
In a direct conversion of primary and secondary alcohols into the corresponding
α-chloro aldehydes and α-chloro ketones, trichloroisocyanuric acid serves both
as stoichiometric oxidant and α-halogenating reagent. For primary alcohols,
TEMPO has to be added as an oxidation catalyst, and for the transformation of
secondary alcohols MeOH as an additive is essential to
promote chlorination of the intermediary ketones.
Y. Jing, C. G. Daniliuc, A. Studer, Org. Lett.,
2014,
16, 4932-4935.
The combination of trichloroisocyanuric acid and cesium fluoride provides acyl
fluorides directly from three different functional group precursors: carboxylic
acids, aldehydes, or alcohols. It can be applied to the late-stage
functionalization of natural products and drug molecules.
Y. Liang, Z. Zhao, A. Taya, N. Shibata, Org. Lett., 2021, 23,
847-852.
A highly convenient organocatalytic method for the mono-oxidation of
unprotected glycosides relies on the chemoselective properties of TEMPO in
combination with trichloroisocyanuric acid under very mild, basic conditions.
The resulting dialdo-glycosides are efficiently purified with the use of
solid-phase imine capture.
M. Angelin, M. Hermansson, H. Dong, O. Ramström, Eur. J. Org. Chem., 2006,
4323-4326.
An efficient one-pot conversion of various alcohols, aldehydes and primary
amines into the corresponding nitriles in excellent yields was easily achieved
by the use of trichloroisocyanuric acid (TCCA) as an oxidant in aqueous ammonia.
Also, various benzylic halides were smoothly and directly converted into the
corresponding aromatic nitriles in high yields under the same conditions.
H. Veisi, Synthesis, 2010,
2631-2635.
An efficient and highly selective method for the oxidative conversion of
primary amines to the corresponding nitriles using trichloroisocyanuric acid
in the presence of catalytic TEMPO provides a new entry to the synthesis of
various aliphatic, aromatic and heterocyclic nitriles in excellent yield.
F.-E. Chen, Y.-Y. Kuang, H.-F. Dai, L. Lu, M. Huo, Synthesis,
2003, 2629-2631.
A mild and metal-free method for the chlorodeboronation of
organotrifluoroborates using trichloroisocyanuric acid (TCICA) converts aryl-,
heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates into the
corresponding chlorinated products in good yields. This method tolerates a broad
range of functional groups.
G. A. Molander, L. N. Cavalcanti, J. Org. Chem., 2011,
76, 7195-7203.
A highly efficient, metal-free, chemical oxidation of hydrazines using
environmentally friendly TCCA as oxidant provides a broad range of azo compounds
in THF in excellent yield. This step-economical process offers mild reaction
conditions, operational simplicity, high reaction efficiency, and easy scale-up.
Y. Su, X. Liu, J. Yu, G. Cao, R. Zhang, Y. Zhao, D. Huang, K.-H. Wang, C. Huo,
Y. Hu, Synthesis, 2020, 52,
1103-1112.
Following a redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine
(TrNSO), the initially formed sulfinamides undergo oxidative chlorination with
trichloroisocyanuric acid to produce sulfonimidoyl chlorides as key
intermediates. Whereas in situ reaction with amines delivers sulfonimidamides,
hydrolysis provides primary sulfonamides.
P. K. T. Lo, M. C. Willis, J. Am. Chem. Soc.,
2021, 143, 15576-15581.
A mechanochemical synthesis of 2,5-disubstituted 1,3,4-oxadiazoles is an
environmentally benign alternative to conventional solvent-based methods. In the
presence of triphenylphosphine and trichloroisocyanuric acid, N-acylbenzotriazoles
condense with acylhydrazides to provide oxadiazoles derivatives in very good
yields within minutes. A range of reactive functionalities was well tolerated.
D. Yamano, N. Wiriya, W. Phakhodee, S. Wet-osot, M. Pattarawarapan, Synlett, 2022,
33,
1458-1462.
