Unexpected Surprise in the Reactions of Acetals and Trialkylsilyl Chloride (R<sub>3</sub>SiCl): Efficient Deprotection of Aromatic Acyclic Acetals

The reaction of acetals with trialkylsilyl chloride (R<sub>3</sub>SiCl) leads to the deprotection of the acetal group, resulting in the corresponding carbonyl compounds. Notably, aromatic dialkyl acetals yield the corresponding parent aromatic aldehydes and ketones in good yields. The reaction conditions are very mild, allowing many acid-labile functional groups to survive without any problems. Additionally, we clarified the reaction mechanism through an NMR study.

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Publication Details

Journal
Chemical and Pharmaceutical Bulletin
Published
2025-04-22
DOI
https://doi.org/10.1248/cpb.c24-00837
Primary Topic
Chemical Synthesis and Reactions
Type
article
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article

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

Shinobu Takizawa, Muthu Karuppasamy, Koji Morimoto, Mohamed S. H. Salem et al.
Chemical and Pharmaceutical Bulletin
Chemical Synthesis and Reactions
article

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

Shinobu Takizawa, Muthu Karuppasamy, Koji Morimoto, Mohamed S. H. Salem, Hiromichi Fujioka, Ishani Uditha Wedage
article en

Abstract

The reaction of acetals with trialkylsilyl chloride (R<sub>3</sub>SiCl) leads to the deprotection of the acetal group, resulting in the corresponding carbonyl compounds. Notably, aromatic dialkyl acetals yield the corresponding parent aromatic aldehydes and ketones in good yields. The reaction conditions are very mild, allowing many acid-labile functional groups to survive without any problems. Additionally, we clarified the reaction mechanism through an NMR study.

Chemical and Pharmaceutical BulletinVol. 73(4)
Suez Canal University (EG), Ritsumeikan University (JP), The University of Osaka (JP)
Openalex Percentile: Top 94%
Chemical Synthesis and Reactions
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Unexpected Surprise in the Reactions of Acetals and Trialkylsilyl Chloride (R&lt;sub&gt;3&lt;/sub&gt;SiCl): Efficient Deprotection of Aromatic Acyclic Acetals — Shinobu Takizawa, Muthu Karuppasamy, et al. · Chemical and Pharmaceutical Bulletin (2025) | TGRS Research Map | TGRS