Trichloroisocyanuric acid (TCCA), an inexpensive, commercially available, and non-toxic reagent has been used for the activation of thioglycosides toward their hydrolysis to the corresponding hemiacetals in high to excellent yields. The methodology provides a mild reaction condition for dealing with compounds containing acid sensitive functional groups.
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http://dx.doi.org/10.1016/j.carres.2013.01.001 | DOI Listing |
Chemistry
January 2025
Université de Montréal, FRQNT Centre in Green Chemistry and Catalysis, Centre for Continuous Flow Synthesis, Department of Chemistry, 1375 av. Thérèse Lavoie-Roux, Montréal, QC, H2V 0B3, Canada.
The pentafluorosulfanyl (SF-) group has been the subject of a surge of interest in the past decade, but there is still little practicality associated with its synthesis and installation. Herein is reported the first continuous flow synthesis of pentafluorosulfanyl chloride (SFCl), the most common reagent for the synthesis of SF-substituted compounds. The synthesis is based on inexpensive and easy-to-handle reagents: sulfur powder (S), trichloroisocyanuric acid (TCCA) and potassium fluoride (KF).
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry, Faculty of Arts and Sciences, Amasya University, Amasya, Turkey.
Herein, a new metal-free, molecular chlorine-free, environmentally friendly, atom-economical, short time, inexpensive and simple operation method with mild reaction conditions for chlorination of alkenes, cyclic alkenes, ,-unsaturated carbonyl compounds, heteroaromatics, and natural products was reported with up to 96% yields using trichloroisocyanuric acid (TCCA) as the electrophilic chlorine source and TBACl as the nucleophilic chlorine source. It was demonstrated with bicyclic alkene benzonorbornadiene that regioselective chlorobromination and dibromination reactions can be carried out through TCCA/TBABr redox reactions, where TCCA acts as an oxidant in the presence of TBABr. The structures of the redox products were confirmed as a result of control experiments conducted with the newly presented DBI/TBACl and DBI/TBABr halogenation pairs.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry and Biochemistry, The University of Tulsa 800 South Tucker Drive, Tulsa, OK 74104, USA.
A variety of dearomatized compounds have been prepared in moderate to excellent yields from planar scaffolds using trichloroisocyanuric acid (TCCA) as an atom-economical chlorinating agent. The method tolerates a broad range of functionalities and can take place in several green and/or sustainable solvents. Twenty-one examples of 1,1-dichlorinated products of dearomatized 2-naphthols and analogous heteroarenes (quinolinols, isoquinolinols, and quinazolinol) are reported along with five examples of monochlorinated dearomatized products.
View Article and Find Full Text PDFJ Org Chem
November 2024
Key Laboratory of Basic Chemistry of the State Ethnic Commission, School of Chemistry and Environment, Southwest Minzu University, Chengdu 610041, P. R. China.
An efficient TCCA (trichloroisocyanuric acid)/RSeSeR-mediated selenoalkoxy of allenamides for the construction of selanyl-allylic N,OA-aminal derivatives was developed. The reaction exhibits good functional group tolerance and high efficiency, affording the products in good to excellent yields. Mechanistic investigations indicated that a selanyl-allylic radical intermediate was first formed via the RSe radical added to the central carbon of allenamides, which subsequently furnished highly stable selanyl-allylic carbocation intermediate by abstraction of an electron by the chlorine radical.
View Article and Find Full Text PDFPhysiol Plant
September 2024
College of Life Sciences, Zhejiang Normal University, Jinhua, P. R. China.
Reactive oxygen species (ROS) have been extensively suggested to stimulate ethylene production. However, the molecular mechanism by which ROS stimulate ethylene production remains largely unclear. Here, transcriptome profiling was used to verify if ROS could stimulate ethylene production via direct formation of ethylene from ROS.
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