DMAPO as Oxidant and Condensing Agent

4-(Dimethylamino)pyridine N-oxide (= DMAPO) is utilized as an oxidant and condensing agent. For example, Yamaguchi et al. reported the efficient conversion of alkyl halides to carbonyl groups by using DMAPO as an oxidant.¹⁾ In this reaction, primary and secondary alkyl halides are used as substrates and can be oxidized to aldehydes and ketones, respectively.
On the other hand, there are reports including improved yields of lactonization by using DMAPO as a condensing agent instead of DMAP²⁾ and amidation in combination with arylboronic acids, which is applicable to less reactive carboxylic acids.³⁾ Furthermore, Sasaki et al. recently reported an amidation reaction using Boc₂O and a catalytic amount of DMAPO. This reaction proceeds under mild conditions in one-pot and is applicable to less reactive amines such as indole and carbazole, so that it is expected to be used in drug discovery research.

Related Products

D3220

4-(Dimethylamino)pyridine N-Oxide (= DMAPO)

D1450

DMAP

D1547

Boc₂O

D1270

1,8-Diazabicyclo[5.4.0]-7-undecene (= DBU)

T0424

Triethylamine

References

• 1) 4-Dimethylaminopyridine N-Oxide as an Efficient Oxidizing Agent for Alkyl Halides
  • S. Mukaiyama, J. Inanaga, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1981, 54, 2221.
• 2) An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones:  A Powerful and Convenient Mixed Anhydride Method Promoted by Basic Catalysts
  • I. Shiina, M. Kubota, H. Oshiumi, M. Hashizume, J. Org. Chem. 2004, 69, 1822.
• 3) Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
  • K. Ishihara, Y. Lu, Chem. Sci. 2016, 7, 1276.
• 4) DMAPO/Boc₂O-Mediated One-Pot Direct N-Acylation of Less Nucleophilic N-Heterocycles with Carboxylic Acids
  • A. Umehara, S. Shimizu, M. Sasaki, ChemCatChem 2023, 15, e202201596.

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