General one-step access to unsymmetric propargylic acetals <i>via</i> alcohol functionalization with allenyl ethers

We report a straightforward and robust protocol for synthesizing unsymmetric propargylic acetals through single-step alkoxypropargylation of aliphatic alcohols. This method employs allenyl ethers and hypervalent iodine reagents to achieve direct functionalization under mild conditions, producing 26 distinct acetals in 60-94% yields. The reaction's broad substrate compatibility accommodates diverse hydroxyl-containing molecules, offering a versatile and scalable platform for installing alkynyl moieties in complex molecular architectures.

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Publication Details

Journal
RSC Advances
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ra01533b
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

General one-step access to unsymmetric propargylic acetals via alcohol functionalization with allenyl ethers

H. C. Liu, Shuzhong He, Yue Yuan, Yang Chen et al.
RSC Advances
Synthetic Organic Chemistry Methods
article

General one-step access to unsymmetric propargylic acetals via alcohol functionalization with allenyl ethers

H. C. Liu, Shuzhong He, Yue Yuan, Yang Chen, Di Li, Bo Yan, Lan Yang, Ai Long
article en

Abstract

We report a straightforward and robust protocol for synthesizing unsymmetric propargylic acetals through single-step alkoxypropargylation of aliphatic alcohols. This method employs allenyl ethers and hypervalent iodine reagents to achieve direct functionalization under mild conditions, producing 26 distinct acetals in 60-94% yields. The reaction's broad substrate compatibility accommodates diverse hydroxyl-containing molecules, offering a versatile and scalable platform for installing alkynyl moieties in complex molecular architectures.

RSC AdvancesVol. 15(15)
Guizhou University (CN)
National Natural Science Foundation of China, Science and Technology Program of Guizhou Province
Openalex Percentile: Top 94%
Synthetic Organic Chemistry Methods
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General one-step access to unsymmetric propargylic acetals <i>via</i> alcohol functionalization with allenyl ethers — H. C. Liu, Shuzhong He, et al. · RSC Advances (2025) | TGRS Research Map | TGRS