Microwave assisted Cobalt(III)-catalysed C-H aminocarbonylation reactions with isocyanates for the synthesis of thiophenecarboxamides

  1. Taboada-Seras, Borja 1
  2. Santiago, Carlos 1
  3. Sustatxa, Eider 1
  4. Carral-Menoyo, Asier 1
  5. Sotomayor, Nuria 1
  6. Lete, Esther 1
  1. 1 Universidad del País Vasco/Euskal Herriko Unibertsitatea
    info
    Universidad del País Vasco/Euskal Herriko Unibertsitatea

    Lejona, España

    ROR https://ror.org/000xsnr85

    Geographic location of the organization Universidad del País Vasco/Euskal Herriko Unibertsitatea
Journal:
ChemRxiv

ISSN: 2573-2293

Year of publication: 2025

Type: Working paper

DOI: 10.26434/CHEMRXIV-2025-4T7Q3 GOOGLE SCHOLAR lock_openOpen access editor

More publications in: ChemRxiv

Abstract

A mild and efficient cobalt(III)-catalysed C-H aminocarbonylation procedure for thiophenes and benzo[b]thiophenes, using pyridine and pyrimidine directing groups to control site selectivity has been developed under MW assisted conditions. The reaction is effective with aromatic isocyanates with wide substitution patterns, although aliphatic isocyanates showed less reactivity. The introduced amide group can act as directing group in further iterative C-H functionalization reactions, allowing the diversification of the heterocyclic structures. DFT calculations have shed light on the mechanistic course and reactivity patterns.

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