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Synthesis 2017; 49(12): 2721-2726
DOI: 10.1055/s-0036-1588755
paper
© Georg Thieme Verlag Stuttgart · New York

Carbodiimides as Acid Scavengers in Aluminum Triiodide Induced Cleavage of Alkyl Aryl Ethers

Dayong Sang
Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei 448000, P. R. of China, Email: tianjuan@jcut.edu.cn
,
Jiahui Wang
Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei 448000, P. R. of China, Email: tianjuan@jcut.edu.cn
,
Yun Zheng
Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei 448000, P. R. of China, Email: tianjuan@jcut.edu.cn
,
Jianyuan He
Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei 448000, P. R. of China, Email: tianjuan@jcut.edu.cn
,
Caili Yuan
Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei 448000, P. R. of China, Email: tianjuan@jcut.edu.cn
,
Qing An
Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei 448000, P. R. of China, Email: tianjuan@jcut.edu.cn
,
Juan Tian*
Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei 448000, P. R. of China, Email: tianjuan@jcut.edu.cn
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Publication History

Received: 23 January 2017

Accepted after revision: 27 February 2017

Publication Date:
14 March 2017 (online)

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Abstract

A practical procedure for the cleavage of alkyl aryl ethers containing labile functional groups has been developed using aluminum triiodide as the ether cleaving reagent. Carbodiimides, typically used as dehydration reagents for the coupling of amines and carboxylic acids to yield amide bonds, are found to be effective hydrogen iodide scavengers that prevent acid-labile groups from deterioration. The method is applicable to variant alkyl aryl ethers such as eugenol, vanillin, ortho-vanillin and methyl eugenol. Suitable substrates are not limited to alkyl o-hydroxyphenyl ethers.

Key words

acid scavenger - aluminum triiodide - carbodiimide - demethylation - ether cleavage

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588755.
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