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Trichloroisocyanuric Acid (TCCA)

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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.


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.