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Visible-Light-Induced Annulation of Benzothioamides with Sulfoxonium Ylides To Construct Thiazole Derivatives.

Org Lett

January 2025

Innovation Center for Chemical Sciences, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou Industrial Park, Suzhou, Jiangsu 215123, China.

Herein, visible-light-induced annulation of benzothioamides with sulfoxonium ylides to furnish thiazole derivatives is developed under transition-metal-, photocatalyst-, and oxidant-free conditions. This protocol exhibits good substrate scope, affording the desired products with satisfied yields in a mild and green manner. Detailed mechanistic studies suggest that the benzothioamide substrate plays a dual role in this reaction.

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Electrochemical synthesis of nitrosation compounds using CHNO as a nitroso reagent.

Chem Commun (Camb)

December 2024

Hefei National Research Center for Physical Sciences at Microscale, Key Laboratory of Precision and Intelligent Chemistry, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China.

An electrochemical synthesis of various nitroso organic compounds (NOCs) from secondary amines was developed under metal-free and oxidant-free conditions. This method used commercially available nitromethane as the nitrosation reagent to provide various NOCs in good to excellent yields. Furthermore, the valuable drug molecule form desloratadine can be prepared by this method easily.

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CeCl-Catalyzed C-H Alkylation of -Sulfonyl Ketimines with Alkanes and Ether via Photoinduced Ligand-to-Metal Charge Transfer.

J Org Chem

December 2024

Green Pharmaceutical Technology Key Laboratory of Luzhou City, School of Pharmacy, Southwest Medical University, Luzhou, Sichuan 646000, P. R. China.

A cerium-catalyzed C-H alkylation of -sulfonyl ketimines with low-cost and readily available alkanes as alkyl sources was developed. This transformation proceeded through the synergy of photoinitiated ligand-to-metal charge transfer (LMCT) using a chlorine radical as an HAT reagent and air as a green oxidant. A series of alkylated -sulfonyl ketimines were synthesized with moderate to good yields in a highly atom-economic manner under chemical oxidant-free conditions.

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Visible light-promoted α-aminoalkyl radical-triggered α-aminoalkylation and α-diaminoalkylation of Morita-Baylis-Hillman acetates with -methyl arylamines to synthesize -containing alkyl acrylates and γ,γ-diaminobutyl esters was reported. Photoinduced α-aminoalkylation is carried out with Na-eosin Y as an organophotocatalyst at room temperature under metal- and oxidant-free conditions. In particular, the α-diaminoalkylation is performed via α-aminoalkyl radical addition/elimination followed by a catalyst-controlled selective α-aminoalkyl radical addition strategy in one step under the [Ir(dtbbpy)(bpy))]PF/KF catalytic system.

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Brook-Oxidation Reaction of Acylsilanes: General Access to α-Ketoamides and α-Ketothioamides.

Org Lett

November 2024

Key Laboratory of Green and Precise Synthetic Chemistry and Application, Ministry of Education, Anhui Provincial Key Laboratory of Synthetic Chemistry and Applications, College of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.

A novel chemoselective Brook-oxidation reaction of acylsilanes initiated by the carbamoyl anion has been successfully developed for the first time. This method enables the synthesis of diverse α-ketoamides and α-ketothioamides under transition metal-free and strong oxidant-free conditions with high yields and high chemoselectivity. It also demonstrates tolerance toward a wide range of functional groups.

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