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2000
Volume 22, Issue 12
  • ISSN: 1570-1786
  • E-ISSN: 1875-6255

Abstract

This study aimed to carry out highly efficient and simple cross-coupling reactions of arylboronic acid with methyl dithiocarbamates for the synthesis of thioamide derivatives using Ni(acac)(5 mol%)/TFP(5 mol%) as a catalyst. Under the optimized reaction conditions, the coupling reaction between arylboronic acid with methyl dithiocarbamates was carried out smoothly, and thioamides were obtained with 27-85% isolated yields. Furthermore, dithiocarbamate methyl esters with allyl, cyano, and acid-sensitive ketal functional groups were successfully coupled with phenylboronic acid to produce the desired product, thioamides, with a yield of 27-69%. Aromatic boronic acids with methoxy or formyl groups on the benzene ring were found to be compatible in this reaction system, and the corresponding thioamides were obtained with an isolated yield of 31-43%. A thioamide with 1-(bis(4-fluorophenyl)methyl)piperazine structural units was prepared with a yield of 65%, which has the potential biological activity. However, this reaction system did not achieve satisfactory results for methyl 1-imidazole-1-carbodithioate. The structures of all the target compounds were confirmed by melting point determination, HMRS, 1H NMR, and 13-CNMR. The broad functional group tolerance and consistent high efficiency at gram-scale synthesis make this protocol a potentially practical approach for producing thioamide derivatives. The method avoids the use of expensive transition metals, such as Pd, Ir, or Rh, and has the advantage of simple operation.

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2025-06-27
2025-12-13

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Nickel-Catalyzed Coupling Reaction of Arylboronic Acid with Methyl Dithiocarbamates for the Synthesis of Thioamides
Lett. Org. Chem. 22, 973 (2025); https://doi.org/10.2174/0115701786318561250619115451
/content/journals/loc/10.2174/0115701786318561250619115451
/content/journals/loc/10.2174/0115701786318561250619115451
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  • Article Type:     Research Article
Keyword(s): arylboronic acid; cross-coupling reaction; methyldithiocarbamates; Nickel catalyst; organic synthesis; thioamides

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