4.8 Article

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Journal

ORGANIC LETTERS
Volume 24, Issue 1, Pages 58-63

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03535

Keywords

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Funding

  1. National Natural Science Foundation of China [21901163]
  2. Shanghai Municipal Education Commission [QD2019024]
  3. Shanghai Engineering Research Center for Food Rapid Detection [19DZ2251300]

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In this study, a Ni-catalyzed reductive transamidation was reported, allowing for the synthesis of various amides with good yields and a broad substrate scope. Furthermore, the same catalytic reaction conditions were applicable for N-sulfonyl benzotriazoles, enabling the synthesis of corresponding sulfonamides.
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

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