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October 16, 2025The Journal of Organic Chemistry6 citations

Cobalt-Catalyzed Amide Bond Formation from Esters and Amines

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XLXiaobin LiXLXiao‐Xiong LvFCFei Chen

Key Points

  • Cobalt complex catalyst efficiently promotes the amidation of esters with amines, achieving 40%-85% yields.
  • Under optimized conditions, minimal racemization occurs with chiral substrates, maintaining ee values of 85-99%.
  • The catalytic system shows high compatibility with diverse substituted methyl benzoates and aromatic amines.
  • This research offers a novel strategy for green and sustainable synthesis of amide bonds from abundant resources.

Abstract

Amide bonds are ubiquitously present in natural products and drug molecules. Traditional methods for constructing amide bonds rely on stoichiometric activating reagents, often leading to the generation of substantial waste. Therefore, the development of green and sustainable synthetic approaches is of significant importance. This study reports a novel cobalt complex catalyst prepared by using inexpensive and readily available CoCl2 as a precursor, which efficiently promotes the amidation of esters with amines. Under optimized reaction conditions (toluene as the solvent, 15 mol % sodium tert-butoxide as the base, 0.6 mol % cobalt complex Cat-1 as the catalyst, 120 °C under a nitrogen atmosphere), the catalytic system exhibits high compatibility with various substituted methyl benzoates, heterocyclic esters, aromatic amines, and secondary amines, delivering products in 40%–85% yields. Notably, it also demonstrates minimal racemization toward chiral substrates with ee values maintained 85–99%. Furthermore, the method has been successfully applied to the synthesis of plant oil-based amide compounds and gram-scale reactions, highlighting its practical utility. This research provides an efficient and atom-economical new strategy for the green synthesis of amide bonds.

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Cite This Study

Li et al. (2025) studied this question.

synapsesocial.com/papers/68f12bfb2107091eab27a4cehttps://doi.org/10.1021/acs.joc.5c01276
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