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Electrochemically Induced Synthesis of -Allyloxyphthalimides via Cross-Dehydrogenative C-O Coupling of -Hydroxyphthalimide with Alkenes Bearing the Allylic Hydrogen Atom.
ACS Omega
December 2024
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russian Federation.
The electrochemically induced reaction between alkenes, bearing an allylic hydrogen atom, and -hydroxyphthalimide was investigated. Cross-dehydrogenative C-O coupling with phthalimide--oxyl radical, derived from -hydroxyphthalimide, occurs instead of oxidation of the allylic site, with the formation of a carbonyl group or functionalization of the double C=C bond. The discovered transformation proceeds in an undivided electrochemical cell equipped with a carbon felt anode and a platinum cathode.
View Article and Find Full Text PDFElectrochemically Induced, Metal Free Synthesis of 2-substituted chroman-4-ones.
ChemistryOpen
November 2024
Institute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924, Łódź, Poland.
Electrochemically induced, decarboxylative functionalization of chromone-3-carboxylic acids by N-hydroxyphthalimide esters as alkyl radical precursors was studied. Electrochemical protocol offers a sustainable and green approach, obviating the need for catalysts, relying on the direct reduction of NHPI esters using electric current. Developed protocol provides a straightforward route to the synthesis of diverse molecules with potential biological activity.
View Article and Find Full Text PDFα-Nucleophilic Addition to α,β-Unsaturated Carbonyl Compounds via Photocatalytically Generated α-Carbonyl Carbocations.
Angew Chem Int Ed Engl
November 2024
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.
We report the photocatalytic oxidation of α-carbonyl radicals of amides or esters to the corresponding α-carbonyl carbocations through super photoreductant CBZ6 induced redox-neutral photocatalysis. The α-carbonyl radicals are formed by the β-addition of alkyl radicals generated in situ by the photocatalytic fragmentation of N-hydroxyphthalimide esters to the α,β-unsaturated amides and esters. This method enables the α-nucleophilic addition of hydroxyl or alkoxyl radicals to amides and esters without any prefunctionalization.
View Article and Find Full Text PDFPhotoinduced Decarboxylative Thioacylation of N-Hydroxyphthalimide Esters with Tetraalkylthiuram Disulfides.
Chemistry
December 2024
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, People's Republic of China.
Dithiocarbamate is a key structural sequence in pharmaceuticals and agrochemicals, and its synthesis is crucial in organic chemistry. Although significant progress has been made in related synthesis research, developing a practical and universal synthesis method remains fascinating. Herein, we report a new visible-light-induced decarboxylation coupling reaction between N-hydroxyphthalimide esters and tetraalkylthiuram disulfides, which uses Ir(ppy) as a photocatalyst to promote the generation of corresponding decarboxylation thioacylation product-dithiocarbamates in high yields.
View Article and Find Full Text PDFVisible-Light-Induced Hydrodifluoromethylation of Unactivated Alkenes with Difluoroacetic Anhydride.
J Org Chem
June 2024
College of Chemistry, Fuzhou University, Fuzhou 350108, China.
We herein described a practical and efficient protocol for hydrodifluoromethylation of unactivated alkenes using readily available difluoroacetic anhydride as a difluoromethyl source by merging photocatalysis and -hydroxyphthalimide activation. This method features a wide substrate scope and excellent compatibility with various functional groups, as demonstrated by more than 50 examples, including bioactive molecules and pharmaceutical derivatives. Mechanism investigation indicated that -hydroxyphthalimide may also serve as the hydrogen atom donor.
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