Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1799-1810.DOI: 10.6023/cjoc202111038 Previous Articles     Next Articles

ARTICLES

钴催化的1-萘胺衍生物与α-羰基羧酸的脱羰C(8)-位酰氧基化反应

王朝彧, 董书达, 朱天阳, 刘玉琴, 武梓涵, 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:2021-11-25 修回日期:2022-01-14 发布日期:2022-02-17
  • 通讯作者: 冯若昆
  • 基金资助:
    浙江省自然科学基金(LQ15B020002); 绍兴市科技计划(2018C10017); 国家级大学生创新创业训练计划(201910349019)

Cobalt-Catalyzed Decarbonylative C(8)-Acyloxylation of 1-Naphthalamine Derivatives with α-Oxocarboxylic Acids

Chaoyu Wang, Shuda Dong, Tianyang Zhu, Yuqin Liu, Zihan Wu, Ruokun Feng()   

  1. Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang 312000
  • Received:2021-11-25 Revised:2022-01-14 Published:2022-02-17
  • Contact: Ruokun Feng
  • Supported by:
    Zhejiang Provincial Natural Science Foundation(LQ15B020002); Shaoxing Science and Technology Plan Project(2018C10017); National College Students' Innovation and Entrepreneurship Training Program(201910349019)

The cobalt-catalyzed decarbonylative C(8)-acyloxylation of 1-naphthalamine derivatives with α-oxocarboxylic acids in the presence of Ag2CO3 and Na2CO3 was developed. Various substituted phenylglyoxylic acids, naphthalenylglyoxylic acid and 2-oxo-2-(thiophen-2-yl)acetic acid can be tolerated in this reaction, giving the desired products in moderate yields. In addition, when deuterated allyl glyoxylic acid is used, the yield of isotope labeled aromatic esterification product is 62%.

Key words: cobalt-catalyzed, C—H activation, 1-naphthylamide, α-oxocarboxylic acids, C(8)-acyloxylation