Unexpected Surprise in the Reactions of Acetals and Trialkylsilyl Chloride (R₃SiCl): Efficient Deprotection of Aromatic Acyclic Acetals

• Material Type: 記事
• Title: Unexpected Surprise in the Reactions of Acetals and Trialkylsilyl Chloride (R₃SiCl): Efficient Deprotection of Aromatic Acyclic Acetals
• Author Heading: Karuppasamy Muthu; Wedage Ishani Uditha; Salem Mohamed S. H.; Morimoto Koji; Takizawa Shinobu; Fujioka Hiromichi
• Publication Date: 2025-04-23
• Publication Date (W3CDTF): 2025-04-23
• Periodical title: Ｃｈｅｍ． Ｐｈａｒｍ． Ｂｕｌｌ．
• No. or year of volume/issue: 73 4
• Volume: 73
• Issue: 4
• Pages: 396-400
• Publication date of volume/issue (W3CDTF): 2025-04-23
• ISSN (Periodical Title): 00092363
• Publication (Periodical Title): The Pharmaceutical Society of Japan
• Text Language Code: en
• Subject Heading: deprotection; aromatic dialkyl acetal; trialkylsilyl chloride; aromatic aldehyde; reaction mechanism
• Target Audience: 一般
• DOI: 10.1248/cpb.c24-00837; https://doi.org/10.1248/cpb.c24-00837
• Related Material (URI): https://www.jstage.jst.go.jp/article/cpb/73/4/73_c24-00837/_pdf
• References: A Simple and Versatile Method for the Formation of Acetals/Ketals Using Trace Conventional Acids; https://cir.nii.ac.jp/crid/1360023717680638976; Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH ₃ CN; https://cir.nii.ac.jp/crid/1360023718866523648; Ruthenium(III) chloride-catalyzed chemoselective synthesis of acetals from aldehydes; https://cir.nii.ac.jp/crid/1360292619506451328; Highly Discriminative and Chemoselective Deprotection/Transformations of Acetals with the Combination of Trialkylsilyl Triflate/2,4,6-Collidine; https://cir.nii.ac.jp/crid/1360567183084685952; <i>N</i>-Bromosuccinimide (NBS) Catalyzed Highly Chemoselective Acetalization of Carbonyl Compounds Using Silylated Diols and Pentaerythritol under Neutral Aprotic Conditions; https://cir.nii.ac.jp/crid/1360586666685730304; Intermolecular Reactions of Chlorohydrine Anions: Acetalization of Carbonyl Compounds under Basic Conditions; https://cir.nii.ac.jp/crid/1360586668671234048; An efficient protection of carbonyls and deprotection of acetals using decaborane; https://cir.nii.ac.jp/crid/1360586670780050560; A Facile Method for the Cleavage of Acetals by the Combined Use of Samarium Trichloride and Chlorotrimethylsilane; https://cir.nii.ac.jp/crid/1360846644038272768; Greene's Protective Groups in Organic Synthesis; https://cir.nii.ac.jp/crid/1361418519222987008; Highly atom efficient aluminium triflate catalysed acetal formation; https://cir.nii.ac.jp/crid/1361699993699156864; Reaction of the Acetals with TESOTf−Base Combination; Speculation of the Intermediates and Efficient Mixed Acetal Formation; https://cir.nii.ac.jp/crid/1362262943683701760; Non-aqueous conversion of ketals to ketones via treatment with trimethylsilyl iodide; https://cir.nii.ac.jp/crid/1362544418685890432; A Simple, Efficient and General Procedure for Acetalization of Carbonyl Compounds and Deprotection of Acetals under the Catalysis of Indium(III) Chloride; https://cir.nii.ac.jp/crid/1364233270422582400; Development of New Innovative Synthetic Organic Chemistry Using Lone Pairs of Oxygen Atoms; https://cir.nii.ac.jp/crid/1390004222629934336
• Data Provider (Database): 国立情報学研究所 : CiNii Research; https://cir.nii.ac.jp/
• Original Data Provider (Database): Japan Link Center; https://japanlinkcenter.org/top; Crossref; https://www.crossref.org; 科学研究費助成事業データベース; https://kaken.nii.ac.jp/ja

• Summary, etc.: <p>The reaction of acetals with trialkylsilyl chloride (R₃SiCl) leads to the deprotection of the acetal group, resulting in the correspondi...