Deprotection of N-Acyl Indole-Type Amides Based on Si-O Bond Cleavage

doi:10.6023/cjoc202510032

Chinese Journal of Organic Chemistry

ARTICLE

基于硅氧键断裂的N-酰基吲哚类酰胺的脱保护

杨鹏飞^*, 马雨婷, 徐婉欣, 孙雨蒙, 仰海凌

蚌埠学院材料与化学工程学院安徽蚌埠 233030

收稿日期:2025-10-30 修回日期:2026-01-22
基金资助:
安徽省自然科学基金(No. 2408085QB050, 2408085MB022)和蚌埠学院高层次人才科研启动基金(No. 2024YYX43QD)资助项目.

Deprotection of N-Acyl Indole-Type Amides Based on Si-O Bond Cleavage

Yang Peng-Fei^*, Ma Yu-Ting, Xu Wan-Xin, Sun Yu-Meng, Yang Hai-Ling

College of Materials Science and Chemical Engineering, Bengbu University, Bengbu, Anhui 233030

Received:2025-10-30 Revised:2026-01-22
Contact: ^*E-mail: PengFeiYang_BBU@163.com
Supported by:
Anhui Provincial Natural Science Foundation (No. 2408085QB050, 2408085MB022) and the Bengbu University High-level Talents Research Start-up Foundation (No. 2024YYX43QD)

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Abstract

The protecting group strategy represents a pivotal approach in organic synthesis, wherein the deprotection of amides has garnered considerable attention. However, due to the high stability of the amide bond, harsh conditions are often required for the deprotection of amides. A method for deprotection of amides under mild conditions has been developed, namely the silane-promoted deprotection of N-acyl indole type amides. The Si-O bond of silane undergoes cleavage, generating a nucleophile in situ that attacks the amide bond, thereby successfully achieving the deprotection of amides. The mild conditions, broad substrate scope, operational simplicity, high yields, and the use of inexpensive and readily available reagents, makes this protocol a green and practical strategy for deprotection of amides.

Key words: N-acyl indole-type amide, Si-O bond cleavage, deprotection, green synthesis

Cite this article

Yang Peng-Fei, Ma Yu-Ting, Xu Wan-Xin, Sun Yu-Meng, Yang Hai-Ling. Deprotection of N-Acyl Indole-Type Amides Based on Si-O Bond Cleavage[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202510032.

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基于硅氧键断裂的N-酰基吲哚类酰胺的脱保护

Deprotection of N-Acyl Indole-Type Amides Based on Si-O Bond Cleavage

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