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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 6: 1799 - 1810

DOI: https://doi.org/10.6023/cjoc202111038

ARTICLES

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
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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
*E-mail:

Received date: 2021-11-25

  Revised date: 2022-01-14

  Online published: 2022-02-18

Supported by

Zhejiang Provincial Natural Science Foundation(LQ15B020002); Shaoxing Science and Technology Plan Project(2018C10017); National College Students' Innovation and Entrepreneurship Training Program(201910349019)

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Abstract

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

Cite this article

Chaoyu Wang , Shuda Dong , Tianyang Zhu , Yuqin Liu , Zihan Wu , Ruokun Feng . Cobalt-Catalyzed Decarbonylative C(8)-Acyloxylation of 1-Naphthalamine Derivatives with α-Oxocarboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1799 -1810 . DOI: 10.6023/cjoc202111038

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