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2020 , Vol. 40 >Issue 3: 714 - 723

DOI: https://doi.org/10.6023/cjoc201908040

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
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  • 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

  网络出版日期: 2019-11-07

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.

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

  • Zhang Mengfan ,
  • Li Ruipeng ,
  • Yang Zhen ,
  • Feng Ruokun
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  • Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang 312000

Received date: 2019-08-30

  Revised date: 2019-10-21

  Online 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

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

本文引用格式

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 . DOI: 10.6023/cjoc201908040

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

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