4.8 Article

Dark and Light Reactions of Carbenes-Merging Carbene Transfer Reactions with N-Heterocyclic Carbene Catalysis for the Synthesis of Hydroxamic Acid Esters

Journal

ACS CATALYSIS
Volume 12, Issue 18, Pages 11129-11136

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c02875

Keywords

carbene transfer reactions; carbene catalysis; photochemistry; diazoalkane; hydroxamic acid; computational studies

Funding

  1. National Natural Science Foundation of China [21971001, 22101002, 21701001]
  2. Fonds der Chemischen Industrie

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In this study, we reported the visible light and N-heterocyclic carbene (NHC) jointly promoted multicomponent carbene transfer reactions. Two kinds of important hydroxamic acid esters were obtained in good yields under optimized reaction conditions depending on the reaction media used. The utility and practicality of this method were demonstrated through mild reaction conditions, excellent functional group tolerance, useful synthetic transformations, and successful modification of natural products and drug molecules.
Herein, we report visible light and N-heterocyclic carbene (NHC) jointly promoted multicomponent carbene transfer reactions. Under the optimized reaction conditions, two kinds of important hydroxamic acid esters were obtained in good yields depending on the reaction media used. The key to this success was driven by the blue light-promoted generation of free carbene species and the fast in situ formation of hydroxamic acid under NHC-catalyzed conditions. The mild reaction conditions, excellent functional group tolerance, useful synthetic transformations, and successful modification of natural products and drug molecules proved the utility and practicality of this method.

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