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Synthesis 2025; 57(19): 2800-2806
DOI: 10.1055/a-2623-7637
Paper

Imidazolium-Based Acid Catalysts for Deacetylation and Debenzoylation

Authors

  • Wen-Yueh Ho‡

    1   Department of Food & Drug Industry and Inspective Technology, Chia Nan University of Pharmacy and Science, Tainan City, Taiwan

  • Amit Pantawane  ‡

    2   Department of Chemistry, National Chung Hsing University, Taichung, Taiwan

  • Qiao Tsai

    2   Department of Chemistry, National Chung Hsing University, Taichung, Taiwan

  • Meng-Jie Yang

    2   Department of Chemistry, National Chung Hsing University, Taichung, Taiwan

  • Sheng-Chieh Yen

    2   Department of Chemistry, National Chung Hsing University, Taichung, Taiwan

  • Jyun-Siao Chen

    2   Department of Chemistry, National Chung Hsing University, Taichung, Taiwan

  • Julakanti Satyanarayana Reddy

    3   Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Zhunan, Taiwan

  • Hsin-Ru Wu

    4   Instrumentation Center, MOST, National Tsing Hua University, Hsinchu, Taiwan

  • Shun-Yuan Luo 

    2   Department of Chemistry, National Chung Hsing University, Taichung, Taiwan

Funding Information The authors thank the National Science and Technology Council, Taiwan (NSTC 112-2113-M-005-008- for S.-Y.L. and NSTC 112-2221-E-041-001- for W.-Y.H.), National Chung Hsing University, and Chia Nan University of Pharmacy and Science for financial support.
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Abstract

Herein, we report a simple and efficient protocol for the deprotection of acetate and benzoate to alcohols, catalyzed by an imidazolium-based acid. Acetate groups were selectively removed while benzoate groups remained intact under mild conditions, and benzoate needed harsher conditions. Notably, this protocol was successfully employed for carbohydrate-building block synthesis in a one-pot strategy, was compatible with different ester protecting groups such as O-Bz, O-Ts, and O-Piv and site-selective deprotection of acetate. The reusable, environmentally benign catalyst enabled smooth operation, resulting in a promising protocol for deprotection.

Key words

Deacetylation - Imidazolium catalyst - Acid catalyst - Debenzoylation - Reuse of catalyst

Supplementary Material



Publication History

Received: 12 March 2025

Accepted after revision: 21 May 2025

Article published online:
31 July 2025

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