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

doi:10.6023/cjoc201908040

有机化学 ›› 2020, Vol. 40 ›› Issue (3): 714-723.DOI: 10.6023/cjoc201908040 上一篇下一篇

研究论文

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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摘要/Abstract

研究了吡啶酰胺双齿导向的钴催化1-萘胺衍生物的区域选择性碳氢键烷氧基化反应.研究发现不仅一元醇可以作为烷氧化剂在标准条件下较好地实现1-萘胺C（8）位的烷氧化反应，而且具有多重用途的脂肪二元醇以及低聚乙二醇，也可以以中等的收率得到相应的目标化合物，这可能是钴催化碳氢键活化构筑碳氧键的首次发现.此外，利用这个实验方法，以氘代甲醇为烷氧化试剂实现了同位素标记的8-烷氧基取代的1-萘胺衍生物的合成.通过控制实验，发现该反应中吡啶酰基是最佳的双导向基团，而且反应过程可能经历了单电子转移机理.

关键词: 钴催化, 双导向, 1-萘胺, C (8)-烷氧化, 区域选择性

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

引用此文

张梦帆, 李瑞鹏, 杨震, 冯若昆. 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[J]. 有机化学, 2020, 40(3): 714-723.

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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