The facile and clean oxidative coupling reaction of pyrroles with azoles has been achieved using the recyclable hypervalent iodine(III) reagents having adamantane structures. These iodine(III) reagents could be recovered from the reaction mixtures by a simple solid-liquid separation, i.e., filtration, for reuse.
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http://dx.doi.org/10.1248/cpb.c15-00469 | DOI Listing |
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.
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February 2024
Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
Electrochemically generated hypervalent iodine(III) species are powerful reagents for oxidative C-N coupling reactions, providing access to valuable N-heterocycles. A new electrocatalytic hypervalent iodine(III)-mediated in-cell synthesis of 1H-N-aryl-3,4-dihydroquinolin-2-ones by dehydrogenative C-N bond formation is presented. Catalytic amounts of the redox mediator, a low supporting electrolyte concentration and recycling of the solvent used make this method a sustainable alternative to electrochemical ex-cell or conventional approaches.
View Article and Find Full Text PDFChem Soc Rev
September 2022
School of Chemistry, Cardiff University, Cardiff, UK.
Hypervalent iodine compounds as environmentally friendly and relatively inexpensive reagents have properties similar to transition metals. They are employed as alternatives to transition metal catalysts in organic synthesis as mild, nontoxic, selective and recyclable catalytic reagents. Formation of C-N, C-O, C-S, C-F and C-C bonds can be seamlessly accomplished by hypervalent iodine catalysed oxidative functionalisations.
View Article and Find Full Text PDFChem Commun (Camb)
January 2022
Chemistry Department, Case Western Reserve University, Cleveland, OH, 44106, USA.
A bulky 1,4-di-iodobenzene having four adjacent -Bu-CH group (Ar') substituents (1) was used to prepare the di-hypervalent iodine compound 1,4-[I(OAc)]-2,3,5,6-Ar'-C (2). Despite the steric encumbrance of the iodine center by the flanking aryl substituents, compound 2 undergoes ready cyclization under mild conditions (excess CFCOOH at 55 °C, 30 min) to afford a dicyclic di-iodonium di-triflate salt 3. The single crystal structures of compounds 2 and 3 were examined and compared to the formerly characterized precursor 1.
View Article and Find Full Text PDFFront Chem
September 2021
Department of Chemistry, Faculty of Chemical and Life Sciences, Abdul Wali Khan University, Mardan, Pakistan.
Chemical synthesis based on Group-Assisted Purification chemistry (GAP) has been prolifically used as a powerful, greener and ecofriendly tool so far. Herein, we report hypervalent iodine (III) mediated regio- and diastereoselective aminobromination of electron-deficient olefins using group-assisted purification (GAP) method. By simply mixing the GAP auxiliary-anchored substrates with TsNH-NBS as nitrogen/bromine sources and PhI(OAc) as a catalyst, a series of vicinal bromoamines with multifunctionalities were obtained in moderate to excellent yields (53-94%).
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