Citation: 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. doi: 10.6023/cjoc201908040 shu

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

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

Corresponding author: Yang Zhen, fengshenghm@usx.edu.cn Feng Ruokun, 33168466@qq.com
Received Date: 30 August 2019
Revised Date: 21 October 2019
Available Online: 7 November 2019
Fund Project: the Shaoxing Science and Technology Plan Project 2018C10017the Zhejiang Provincial Natural Science Foundation LQ15B020002Project supported by the Zhejiang Provincial Natural Science Foundation (No. LQ15B020002) and the Shaoxing Science and Technology Plan Project (No. 2018C10017)

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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.
- cobalt-catalyzed,
- bidentate-assisted,
- 1-naphthylamide,
- C (8)-alkoxylation,
- regioselectivity
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