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Author:

Liu, Li (Liu, Li.) | Wang, Jing (Wang, Jing.) | Feng, Xiaoying (Feng, Xiaoying.) | Xu, Kun (Xu, Kun.) | Liu, Wei (Liu, Wei.) | Peng, Xia (Peng, Xia.) | Du, Hongguang (Du, Hongguang.) | Tan, Jiajing (Tan, Jiajing.)

Indexed by:

Scopus SCIE

Abstract:

A visible-light-enabled, photocatalyst-free hydroacylation reaction of azodicarboxylic acid derivatives was described. This radical conjugate addition (RCA) protocol relied on the dual role of 4-acyl-1,4-dihydropyridine (acyl-DHP) reagents that besides being as radical reservoirs, they also enabled the conversion of radical adducts to anion intermediates via reduction. Under "catalyst-oxidant-additive free" conditions, a wide range of structurally different acyl hydrazide products were readily obtained in 56%-99% yields. The utility of this transformation was further demonstrated by the scale-up synthesis and downstream derivatization.

Keyword:

4-Acyl-1,4-dihydropyridine Azo compounds Radicals Photochemistry Acylation

Author Community:

  • [ 1 ] [Liu, Li]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China
  • [ 2 ] [Wang, Jing]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China
  • [ 3 ] [Feng, Xiaoying]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China
  • [ 4 ] [Liu, Wei]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China
  • [ 5 ] [Peng, Xia]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China
  • [ 6 ] [Du, Hongguang]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China
  • [ 7 ] [Tan, Jiajing]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China
  • [ 8 ] [Liu, Li]Sinopec Beijing Res Inst Chem Ind, Beijing 100013, Peoples R China
  • [ 9 ] [Xu, Kun]Beijing Univ Technol, Fac Environm & Life, Beijing 100124, Peoples R China

Reprint Author's Address:

  • [Du, Hongguang]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China;;[Tan, Jiajing]Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China;;[Xu, Kun]Beijing Univ Technol, Fac Environm & Life, Beijing 100124, Peoples R China

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Source :

CHINESE JOURNAL OF CHEMISTRY

ISSN: 1001-604X

Year: 2024

Issue: 11

Volume: 42

Page: 1230-1236

5 . 4 0 0

JCR@2022

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count:

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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