杂芳基烷基醚、杂芳基卤化物与(氘代)醇的亲核醚化

doi:10.6023/cjoc202006077

有机化学 ›› 2021, Vol. 41 ›› Issue (2): 795-805.DOI: 10.6023/cjoc202006077 上一篇下一篇

研究论文

杂芳基烷基醚、杂芳基卤化物与(氘代)醇的亲核醚化

王霞¹, 屈益欣¹, 龙城宇¹, 王雪强¹^,^*()

1 湖南大学化学化工学院分子科学与生物医学实验室(MBL) 化学/生物传感与化学计量家重点实验室长沙 410082

收稿日期:2020-06-30 修回日期:2020-08-20 发布日期:2020-10-12
通讯作者: 王雪强
作者简介:
* Corresponding author. E-mail: wangxq@hnu.edu.cn
† 共同第一作者(These authors contributed equally to this work).
基金资助:
湖南省湖湘青年人才计划(2019RS2022)

Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols

Xia Wang¹, Yixin Qu¹, Chengyu Long¹, Xue-Qiang Wang¹^,^*()

1 Molecular Science and Biomedicine Laboratory, State Key Laboratory of Chemo/Bio-sensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2020-06-30 Revised:2020-08-20 Published:2020-10-12
Contact: Xue-Qiang Wang
Supported by:
the Huxiang Young Talent Program from Hunan Province(2019RS2022)

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1. cjoc20206077辅助材料.pdf(6638KB)

摘要/Abstract

研究了在叔丁醇钾的作用下, 杂芳基烷氧化合物、杂芳基卤化物和杂芳基硫醚与各种伯、仲、叔脂肪醇高效醚化, 强调了天然产物和生物活性分子的衍生化以及不易通过其他途径获得的氘代芳基烷基醚的合成方法的实用性.

关键词: 醚化, 杂芳基烷基醚, 芳香亲核取代

A KOt-Bu empowered transition-metal free and efficient procedure for the etherification of alkoxy heteroarenes, heteroaryl halides and heteroaryl thioethers with various primary, secondary, tertiary aliphatic alcohols has been developed. The usefulness of our method is highlighted by the derivatization of natural products and bioactive molecules, and the synthesis of deuterated heteroaryl alkyl ethers that are not easy to access via other approaches.

Key words: etherification, heteroaryl alkyl ethers, nucleophilic aromatic substitution

引用此文

王霞, 屈益欣, 龙城宇, 王雪强. 杂芳基烷基醚、杂芳基卤化物与(氘代)醇的亲核醚化[J]. 有机化学, 2021, 41(2): 795-805.

Xia Wang, Yixin Qu, Chengyu Long, Xue-Qiang Wang. Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 795-805.

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图/表 5

Figure 1. Representative ether containing anticancer drugs and the methods for heteroaryl ether synthesis.

Table 1. Scope of nucleofugesa

Table 2. Scope of methoxy heteroarenes and alcohols

Table 3. Derivatization of pharmaceuticals or bio-related molecules

Table 4. Scope of etherification of deuterated alcoholsa

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杂芳基烷基醚、杂芳基卤化物与(氘代)醇的亲核醚化

Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols

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