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

Direct transamidation of secondary amides was developed via nickel catalysis. In the presence of trimethylsilyl chloride and manganese, Ni­(diglyme)­Cl2 with a Briphos ligand efficiently promoted the transamidation of N-aryl benzamide derivatives with primary amines to afford the corresponding secon...

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Bibliographic Details
Published in:Organic letters 2018-12, Vol.20 (23), p.7563-7566
Main Authors: Yu, Subeen, Shin, Taeil, Zhang, Maosheng, Xia, Yuanzhi, Kim, Hyunwoo, Lee, Sunwoo
Format: Article
Language:English
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Summary:Direct transamidation of secondary amides was developed via nickel catalysis. In the presence of trimethylsilyl chloride and manganese, Ni­(diglyme)­Cl2 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03304