Dehydrative condensation of carboxylic acids and amines is the primary option for the synthesis of amides. Given the ubiquitous nature of amide bond linkages, competent amidation catalysts have long been sought after for enabling general amide synthesis. A research group in the Institute of Microbial Chemistry (Tokyo) developed the Pym-DATB catalyst (901627) featuring a B3NO2 heterocycle, which engages a wide range of carboxylic acids and amines in amide bond formation.

Pym-DATB Amidation Catalyst

Figure 1. Pym-DATB Amidation Catalyst (901627)

Advantages Pym-DATB Amidation Catalyst

  • Non-hygroscopic bench-stable solid
  • High functional group tolerance(alcoholic/phenolic–OH; –SH; N-Boc/acetal/tBu ester/heteroaromatic N)
  • Broad substrate generality(α-disubstituted carboxylic acids; aromatic carboxylic acids; secondary amines; anilines)

Scope of Pym-DATB Catalyst

Reaction condition: catalyst 1 - 5 mol% in PhF or toluene

Scope of Pym-DATB Catalyst

Figure 2.Scope of Pym-DATB Catalyst

General Procedure Dehydrative Condensation of Carboxylic Acids

  1. A flask is charged with amine and acid(1:1, 0.25 mmol)and Pym-DATB(5 mol%), before
    fluorobenzene(reagent grade, 5 mL)is added.
  2. A Soxhlet extractor containing 4Å molecular sieves(beads,1.5 g)and water-jacketed reflux condenser are attached,
    and the mixture is refluxed (85 °C) for 8–16 h. The catalyst may remain partly undissolved.
  3. The resulting mixture is concentrated and suspended with chloroform (10 mL). Filtration through Celite removes the bulk of the catalyst, and concentration of the filtrate give amide product.

*The use of toluene with Dean-Stalk apparatus can obviate the use of molecular sieves.

Materials
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References

1.
Opie CR, Noda H, Shibasaki M, Kumagai N. 2019. All Non?Carbon B 3 NO 2 Exotic Heterocycles: Synthesis, Dynamics, and Catalysis. Chem. Eur. J.. 25(18):4648-4653. http://dx.doi.org/10.1002/chem.201900715

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