A ditriflate derivative of 2-iodoxybenzoic acid (IBX) was prepared by the reaction of IBX with trifluoromethanesulfonic acid and characterized by single crystal X-ray crystallography. IBX-ditriflate is the most powerful oxidant in a series of structurally similar IBX derivatives which is best illustrated by its ability to readily oxidize hydrocarbons and the oxidation resistant polyfluoroalcohols.
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http://dx.doi.org/10.1039/c9cc04203b | DOI Listing |
Chemistry
December 2024
Indian Institute of Technology Kanpur, Department of Chemistry, IIT, Kanpur, 208 016, Kanpur, INDIA.
Porous organic polymers (POPs) are novel emergent materials for heterogeneous organocatalysis owing to their remarkable physicochemical stabilities. Through a bottom-up approach entailing diligent design of twisted biaryl building blocks with in-built o-iodobenzoic acid (IA) moieties, a series of POP precatalysts, p-OMeIA-POP, DiMeIA-POP, and m-OMeIA-POP, were synthesized by employing Friedel-Crafts alkylation. These IA-POP precatalysts can undergo in situ oxidation in the presence of Oxone® to generate hypervalent iodine(V) species (λ5-iodanes), in particular, modified o-iodoxybenzoic acid, popularly termed IBX, which mediates diverse oxidative transformations.
View Article and Find Full Text PDFCurr Org Synth
January 2024
Department of Chemistry, Chaitanya Bharathi Institute of Technology (CBIT), Gandipet, Hyderabad, 500075, Telangana, India.
This study reviews the oxidative applications of 2-iodoxybenzoic acid (IBX) in organic synthesis, focusing on C-H functionalization, hetero-hetero bond formations, ring cleavage reactions, dehydrogenation, heterocyclic ring formations, and some miscellaneous reactions in a comprehensive and critical way. It compiles the literature starting from mid-2015 to date.
View Article and Find Full Text PDFOrg Lett
September 2023
School of Chemistry, IISER Trivandrum, Kerala 695551, India.
-Iodoxybenzoic acid (IBX) and Dess-Martin periodinane (DMP) are employed for thiol to thiosulfonate conversion at rt. DMP is better than IBX in terms of reaction rate, conversion, and required equivalents. IBX-mediated oxidation of benzyl thiols produced thiosulfonates, whereas DMP afforded -benzyl esters.
View Article and Find Full Text PDFAdv Mater
September 2023
Joint Key Laboratory of the Ministry of Education, Institute of Applied Physics and Materials Engineering, University of Macau, Taipa, Macau SAR, 999078, China.
Noninvasive fluorescence (FL) imaging and high-performance photocatalytic therapy (PCT) are opposing optical properties that are difficult to combine in a single material system. Herein, a facile approach to introducing oxygen-related defects in carbon dots (CDs) via post-oxidation with 2-iodoxybenzoic acid is reported, in which some nitrogen atoms are substituted by oxygen atoms. Unpaired electrons in these oxygen-related defects rearrange the electronic structure of the oxidized CDs (ox-CDs), resulting in an emerging near-infrared (NIR) absorption band.
View Article and Find Full Text PDFJ Org Chem
October 2022
School of Natural Sciences, University of Tasmania, Private Bag 75, Hobart, Tasmania 7001, Australia.
The 2-iodoxybenzoic acid (IBX)-controlled oxidative dearomatization of pyrroles occurs very slowly (or not all) in many organic solvents, including DMSO in which IBX is soluble. Interestingly, although IBX is only partially soluble in acetic acid, this solvent mediates the pyrrole oxidative dearomatization. With the aid of density functional theory (DFT) calculations, we have discovered a new mode of reactivity, termed the periodinane oxy-assisted (POA) oxidation mechanism, which explains this observation.
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