Dehydrative Couplingof Carboxylic Acids with Aminesin the Presence of Sodium Azepane-1-carbodithioate


Yıldırım A.

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2026 (SCI-Expanded, Scopus)

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2026
  • Doi Numarası: 10.1021/acs.oprd.6c00193
  • Dergi Adı: ORGANIC PROCESS RESEARCH & DEVELOPMENT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Compendex
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

The reaction of a carboxylic acid with an amine in the presence of a catalytic carbodithioate affords the corresponding amide under thermal conditions, excluding the requirement for stoichiometric coupling reagents. The high-yield preparation of amides in the presence of sodium azepane-1-carbodithioate, which can be readily prepared, demonstrates that this agent does not behave as a simple nucleophile but rather plays a critical role in acyl activation and transfer. The advantages of the developed simple catalytic method include minimization of reagents, the ability to operate in a solvent-free environment in many cases, minimal solvent requirement, high product yield, and applicability for scale-up in the synthesis of amides. This method allows for the successful use of various aliphatic and/or aromatic substrates as well as some functionalized carboxylic acids. The study also provided mechanistic insights into the amidation process through Fourier transform infrared analysis and density functional theory calculations.