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An electrochemical Ni-catalyzed reductive cross-coupling of arylcarboxylic esters with alkylpyridinium salts has been developed. Various aryl alkyl ketones are obtained in good to excellent yields (up to 86% yield). The reaction tolerated a variety of primary alkylpyridinium salts, including substrates with protic functional groups and derivatives of bioactive molecules. This method exhibits several synthetic advantages, including high efficiency (reaction time of 1.5 h), the use of easily available alkylpyridinium salts (dual roles as the alkyl source and electrolyte), a convenient procedure (undivided cell), and a wide substrate scope (47 examples). This route provides a novel and efficient method for the synthesis of aryl ketones.
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http://dx.doi.org/10.1021/acs.joc.5c01714 | DOI Listing |
J Org Chem
August 2025
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
An electrochemical Ni-catalyzed reductive cross-coupling of arylcarboxylic esters with alkylpyridinium salts has been developed. Various aryl alkyl ketones are obtained in good to excellent yields (up to 86% yield). The reaction tolerated a variety of primary alkylpyridinium salts, including substrates with protic functional groups and derivatives of bioactive molecules.
View Article and Find Full Text PDFJ Org Chem
September 2024
Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases, Ministry of Education; Jiangxi Provincal Key Laboratory of Tissue Engineering; School of Pharmaceutical Sciences, Gannan Medical University, Ganzhou 341000, PR China.
Divergent synthesis of structurally different products from the same kinds of starting materials is highly synthetically useful but very challenging. Herein, we reported a base-mediated chemodivergent [4 + 1] and [2 + 1] cycloaddition of -alkylpyridinium and enone under mild conditions, leading to furan-fused bicycles with high diastereoselectivity and spirobicycles, respectively, from moderate to high yields. -Alkylpyridinium salts were modular nucleophilic transfer reagents and C1 synthons, which underwent tandem Michael addition to the α,β-unsaturated ketones and cyclization under the base conditions.
View Article and Find Full Text PDFPhytochemistry
April 2024
Research Center for Marine Drugs, Department of Pharmacy, Ren Ji Hospital, School of Medicine, State Key Laboratory of Microbial Metabolism, Shanghai Jiao Tong University, Shanghai, 200127, China.
ACS Catal
July 2023
Discovery Chemistry, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.
An electrochemical, nickel-catalyzed reductive coupling of alkylpyridinium salts and aryl halides is reported. High-throughput experimentation (HTE) was employed for rapid reaction optimization and evaluation of a broad scope of pharmaceutically relevant structurally diverse aryl halides, including complex drug-like substrates. In addition, the transformation is compatible with both primary and secondary alkylpyridinium salts with distinct conditions.
View Article and Find Full Text PDFJ Org Chem
January 2024
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.