New method discovered by Chengdu Biology to catalyze the oxidation of alkynes with oxygen to build amides

Amide functional groups are the basic structural units of proteins, and are one of the most important building blocks for building multifunctional polymers, biomaterials and drug molecules. Traditional amide synthesis methods mainly rely on the condensation reaction of carboxylic acids and their derivatives with amines. Most of them require multiple preparation steps and activation of raw materials, and the reaction conditions are harsh. So far, it has only been found in some biooxygenase systems that oxygen is used as an oxygen source to synthesize amide functional groups. Direct use of metal catalysts, oxygen and simple commercial raw materials to synthesize amides has always been a challenge.

Ji Jianxin's team at the Molecular Structure Diversity Construction and Medicinal Chemistry Laboratory, Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, realized the transition metal-catalyzed oxidation of alkyne to synthesize amide compounds using oxygen. The research group Dr. Wei Wei discussed the reaction mechanism through various methods such as isotope labeling experiment and NMR analysis, and the research confirmed that the oxygen atom in the product amide came from O2. The results of this study were published in Chem. Commun. (DOI: 10.1039 / c1cc14640h).

So far, the research group has developed three new methods for constructing important oxygen-containing organic blocks directly using oxygen as the oxygen source under the copper catalytic system, such as catalytic synthesis of β-carbonyl phosphonate (Angew. Chem. Int. Ed ., 2011, 50, 9097-9099), o-carbonylamide (Chemical Science, DOI: 10.1039 / C1SC00312G, Edge Article) and amide, showing a novel transition metal catalyzed reaction mode of using oxygen to construct oxygenates.

reaction process

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