Diaryliodonium triflates transfer an aryl group to the chalcogen atom of organic sulfides, selenides, and tellurides (but not ethers), in the absence of transition-metal catalyst, simply upon heating in chloroform or dichloroethane solution.
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http://dx.doi.org/10.1021/ol503177q | DOI Listing |
J Org Chem
December 2024
Department of Chemistry, Sidho-Kanho-Birsha University, Purulia 723104, W.B., India.
Distinctive, green, innovative, and well-organized photoinduced (metal- or photocatalyst-free) regioselective decarbonylative and decarboxylative C-O bond functionalization protocols to access aryl 2-aminobenzoates and 2-substituted benzoxazinone derivatives in excellent yields have been devised. These are achieved through the chemoselective scission of isatoic anhydride with ketones, diaryliodonium triflate, nitroalkene, phthalazinone, and phenol derivatives, which, in turn, served as the representative "electrophilic and nucleophilic" coupling partners. Control experiments and DFT calculations reveal that electrophilic radical-bearing coupling partners specifically follow the decarbonylation pathway, while nucleophilic radical-bearing conjugates facilitate the decarboxylation process.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Fluoro-Agrochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.
An efficient and operationally simple photochemical method has been demonstrated under transition metal-free, photocatalyst-free, and oxidant-free conditions. In recent times, diaryliodonium salts have become one of the most popular arylating sources under photoinduced conditions. Herein, we developed a visible light induced arylation of heterocycles using an EDA complex that is formed from 2,6-lutidine and diaryliodonium triflate.
View Article and Find Full Text PDFBeilstein J Org Chem
January 2024
Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, D-28359 Bremen, Germany.
-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in -xylene, using the commonly found activating ligand diglyme. We have tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates.
View Article and Find Full Text PDFOrg Lett
November 2023
Department of Chemistry, Indian Institute of Technology Jodhpur, Karwar-342037, Rajasthan, India.
We report an organophotoredox-catalyzed stereoselective allylic arylation of MBH acetates with a palette of diaryliodonium triflates (DAIRs) to provide the corresponding trisubstituted alkenes in moderate to good yields. The method could be extended to three-component coupling involving 1,4-diazabicyclo[2.2.
View Article and Find Full Text PDFOrg Biomol Chem
July 2023
Department of Chemistry, Indian Institute of Technology Jodhpur, Karwar-342037, Rajasthan, India.
A copper-catalyzed efficient method for the synthesis of a diverse variety of substituted -aryl pyrazoles from readily available α,β-alkynic -tosyl hydrazones and diaryliodonium triflates is realized. This one-pot multi-step methodology features a broad scope with good yields, scalability, and appreciable functional group tolerance. Detailed control experiments reveal that the reaction proceeds through tandem cyclization/deprotection/arylation events where the copper catalyst plays a distinct role.
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