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Heterogeneous Catalytic Oxidations with In Situ-Generated Hypervalent Iodine-Based Porous Organic Polymers.
Chemistry
December 2024
Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, 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 (λ-iodanes), in particular, modified o-iodoxybenzoic acid, popularly termed IBX, which mediates diverse oxidative transformations.
View Article and Find Full Text PDFOxidation of Thiols with IBX or DMP: One-Pot Access to Thiosulfonates or 2-Iodobenzoates and Applications in Functional Group Transformations.
Org 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 PDFIBX-Mediated Organic Transformations in Heterocyclic Chemistry-A Decade Update.
Front Chem
February 2022
Organic Catalysis and Biocatalysis Laboratory-LACOB, Federal University of Grande Dourados-UFGD, Dourados, Brazil.
O-Iodoxybenzoic acid (IBX) is a very mild and efficient hypervalent iodine synthetic reagent useful to carry out several selective oxidations. The present review highlights research reports on IBX-assisted transformations in heterocyclic derivatives, particularly from 2010 onward.
View Article and Find Full Text PDFDirect Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.
J Am Chem Soc
June 2019
Department of Chemistry , Georgia State University, 100 Piedmont Avenue SE , Atlanta Georgia 30303 , United States.
We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.
View Article and Find Full Text PDFDesign and Synthesis of Potent HIV-1 Protease Inhibitors Containing Bicyclic Oxazolidinone Scaffold as the P2 Ligands: Structure-Activity Studies and Biological and X-ray Structural Studies.
J Med Chem
November 2018
Department of Refractory Viral Infections , National Center for Global Health and Medicine Research Institute, Tokyo 162-8655 , Japan.
We have designed, synthesized, and evaluated a new class of potent HIV-1 protease inhibitors with novel bicyclic oxazolidinone derivatives as the P2 ligand. We have developed an enantioselective synthesis of these bicyclic oxazolidinones utilizing a key o-iodoxybenzoic acid mediated cyclization. Several inhibitors displayed good to excellent activity toward HIV-1 protease and significant antiviral activity in MT-4 cells.
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