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


张梦帆, 李瑞鹏, 杨震, 冯若昆   

  1. 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;
  • 基金资助:

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

Zhang Mengfan, Li Ruipeng, Yang Zhen, Feng Ruokun   

  1. 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).

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