Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 50, 2020 - Issue 23

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Transition metal-free S_NAr-type etherification with allyl alcohols: Synthesis of allyl pyridyl ethers

Aiwen Huoa Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Xingzong Wanga Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Xiang Lib Qinhuangdao Customs Technical Center, Qinhuangdao, China

Yan Zhanga Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Yingjie Guoa Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Liyan Zhanga Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Fan Wanga Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Juhui Wanga Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Feng Lia Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Qing Hea Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Hengjie Lianga Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Tengda Jina Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Zhibin Wanga Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, China

Jingyue Yanga Hebei Key Laboratory of Applied Chemistry, School of Environmental and Chemical Engineering, Yanshan University, Qinhuangdao, ChinaCorrespondence[email protected]

https://orcid.org/0000-0003-3080-8732

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Abstract

Allyl pyridyl ethers are important intermediates in organic synthesis, which could be accessed by Williamson or S_NAr-type etherification. While Williamson etherification has been well studied, the S_NAr-type reaction remains less explored. In this paper, a series of allyl pyridyl ethers were synthesized via transition metal-free S_NAr-type etherification with different allyl alcohols in good yields. The poor-yielding etherification for cinnamyl alcohol was finally optimized to 82% yield with a molecular sieve as the additive.

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Acknowledgments

The authors thank the Yanshan University High-end Talents Project: No. BL18014 and the Department of Education of Hebei Province Foundation: No. QN2019220.

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Transition metal-free S_NAr-type etherification with allyl alcohols: Synthesis of allyl pyridyl ethers

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Transition metal-free SNAr-type etherification with allyl alcohols: Synthesis of allyl pyridyl ethers

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Transition metal-free S_NAr-type etherification with allyl alcohols: Synthesis of allyl pyridyl ethers