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Synthesis
DOI: 10.1055/a-2623-7637
paper

Imidazolium-Based Acid Catalysts for Deacetylation and Debenzoylation

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
› Author Affiliations
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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