4.8 Article

Nickel/Briphos-Catalyzed Direct Transamidation of Unactivated Secondary Amides Using Trimethylsilyl Chloride

Journal

ORGANIC LETTERS
Volume 20, Issue 23, Pages 7563-7566

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03304

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Funding

  1. National Research Foundation of Korea (NRF) - Korean government (MSIP) [NRF-2015R1A4A1041036, NRF-2017R1A2B4002650, NRF-2017R1A2B2002929]
  2. National Research Foundation of Korea [2015R1A4A1041036, 2017R1A2B4002650, 2017R1A2B2002929] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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Direct transamidation of secondary amides was developed via nickel catalysis. In the presence of trimethylsilyl chloride and manganese, Ni(diglyme)Cl-2 with a Briphos ligand efficiently promoted the transamidation of N-aryl benzamide derivatives with primary amines to afford the corresponding secondary amides in moderate to good yields. Primary amines bearing electron-donating groups gave higher yields of the transamidation products.

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