Cobalt-Catalyzed Bidentate-Assisted Regioselective C—H Alkoxylation of 1-Naphthylamide with Alcohols

doi:10.6023/cjoc201908040

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 714-723.DOI: 10.6023/cjoc201908040 Previous Articles Next Articles

钴催化双齿导向基辅助的1-萘胺衍生物与醇的区域选择性碳氢键烷氧基化反应

张梦帆, 李瑞鹏, 杨震, 冯若昆

绍兴文理学院化学化工学院浙江省精细化学品传统工艺替代技术研究重点实验室浙江绍兴 312000

收稿日期:2019-08-30 修回日期:2019-10-21 发布日期:2019-11-07
通讯作者: 杨震, 冯若昆 E-mail:fengshenghm@usx.edu.cn;33168466@qq.com
基金资助:
浙江省自然科学基金（No.LQ15B020002）和绍兴市科技计划（No.2018C10017）资助项目.

Cobalt-Catalyzed Bidentate-Assisted Regioselective C—H Alkoxylation of 1-Naphthylamide with Alcohols

Zhang Mengfan, Li Ruipeng, Yang Zhen, Feng Ruokun

Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang 312000

Received:2019-08-30 Revised:2019-10-21 Published:2019-11-07
Supported by:
Project supported by the Zhejiang Provincial Natural Science Foundation (No. LQ15B020002) and the Shaoxing Science and Technology Plan Project (No. 2018C10017).

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Abstract

The cobalt-catalyzed regioselective C-H alkoxylation of 1-naphthylamide with alcohols through a bidentate-chelation assistance has been developed. In this transformation, not only primary and secondary alcohols, but also aliphatic diols and oligoethylene glycols, which always be employed as O,O-donor ligands and reducing agents in transition metal catalyzed coupling reaction, were all tolerated under current reaction conditions. It is noteworthy that deuterium labeled 8-alkoxyl-1-N-(naphthalen-1-yl)picolinamide derivative was easily achieved under this catalytic system. In addition, control experiments suggested that picolinoyl was the key directing group, and furthermore, the C(8)-H alkoxylation reaction might proceed through a single-electron-transfer (SET) process.

Key words: cobalt-catalyzed, bidentate-assisted, 1-naphthylamide, C (8)-alkoxylation, regioselectivity

Cite this article

Zhang Mengfan, Li Ruipeng, Yang Zhen, Feng Ruokun. Cobalt-Catalyzed Bidentate-Assisted Regioselective C—H Alkoxylation of 1-Naphthylamide with Alcohols[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 714-723.

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钴催化双齿导向基辅助的1-萘胺衍生物与醇的区域选择性碳氢键烷氧基化反应

Cobalt-Catalyzed Bidentate-Assisted Regioselective C—H Alkoxylation of 1-Naphthylamide with Alcohols

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