A silver-catalyzed decarboxylative trifluoromethylthiolation of secondary and tertiary carboxylic acids under mild conditions tolerates a wide range of functional groups. The reaction was dramatically accelerated by its performance in an aqueous emulsion, which was formed by the addition of sodium dodecyl sulfate to water. It was proposed that the radical, which was generated from the silver-catalyzed decarboxylation in the "oil-in-water" droplets, could easily react with the trifluoromethylthiolating reagent to form the product.
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http://dx.doi.org/10.1002/anie.201402573 | DOI Listing |
Org Lett
October 2024
Department of Analytical & Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Here we report the development of unprecedented silver-catalyzed intramolecular annulations of -acrolyl-2-(3-indolyl) benzimidazoles with alkyl carboxylic acids to construct complex fused-pentacyclic alkaloid scaffolds. Divergent reactivities are noticed with altered groups at C2-indole of the substrate. The reaction proceeds through decarboxylative alkylation, followed by dearomative annulation in a domino manner with excellent diastereoselectivity.
View Article and Find Full Text PDFOrg Biomol Chem
August 2024
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India.
An unprecedented radical-promoted strategy involving a domino alkylation/intramolecular C5-annulation of -acryloyl-4-amino coumarin has been devised for the assembly of 4,5-fused coumarin scaffolds. This protocol employs silver-catalyzed oxidative decarboxylation for the generation of alkyl radicals from carboxylic acids, which were used as radical precursors. This method has also been extended to a diverse range of carbon-centered radicals generated from 2-oxo acids, a 1,3-dicarbonyl compound, isopropanol and acetone.
View Article and Find Full Text PDFOrg Lett
July 2024
College of Chemistry and Chemical Engineering, State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha, Hunan 410082, China.
Org Lett
April 2024
School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.
Herein, we report a silver-catalyzed protocol for decarboxylative cross-coupling between carboxylic acids and isocyanides, leading to linear amide products through a free-radical mechanism. The disclosed approach provides a general entry to a variety of decorated amides, accommodating a diverse array of radical precursors, including aryl, heteroaryl, alkynyl, alkenyl, and alkyl carboxylic acids. Notably, the protocol proved to be efficient for decarboxylative late-stage functionalization of several elaborate pharmaceuticals, demonstrating its potential applications.
View Article and Find Full Text PDFOrg Lett
March 2024
Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
A silver-catalyzed decarboxylative remote fluorination via a zwitterion-promoted 1,4-heteroaryl migration has been developed. A variety of heteroaryl-tethered benzyl fluorides have been readily synthesized with good regioselectivity under mild conditions. The zwitterion of the substrate is suggested to accelerate the 1,4-heteroaryl migration, which determines the regioselectivity of this transformation.
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