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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 23
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Articles

Transition metal-free SNAr-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]
ORCID Iconhttps://orcid.org/0000-0003-3080-8732
ORCID Icon show all
Pages 3669-3675 | Received 19 Feb 2020, Published online: 08 Sep 2020
 
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Abstract

Allyl pyridyl ethers are important intermediates in organic synthesis, which could be accessed by Williamson or SNAr-type etherification. While Williamson etherification has been well studied, the SNAr-type reaction remains less explored. In this paper, a series of allyl pyridyl ethers were synthesized via transition metal-free SNAr-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.

Graphical Abstract

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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