Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N-Acylsaccharins

Shengzhang Liu; Lingyun Yang; Jiasi Tao; Weijie Yu; Tao Wang; Junkai Fu

doi:10.1055/a-1517-5895

Synlett, Table of Contents

Synlett 2021; 32(16): 1642-1646
DOI: 10.1055/a-1517-5895

cluster

Modern Nickel-Catalyzed Reactions

Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N-Acylsaccharins

Shengzhang Liu‡

^aCollege of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

,

Lingyun Yang‡

^aCollege of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

,

Jiasi Tao

^aCollege of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

,

Weijie Yu

^aCollege of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

,

Tao Wang∗

^aCollege of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

^bNational Research Center for Carbohydrate Synthesis, Jiangxi Province’s Key Laboratory of Chemical Biology, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

,

Junkai Fu ∗

^aCollege of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

^bNational Research Center for Carbohydrate Synthesis, Jiangxi Province’s Key Laboratory of Chemical Biology, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

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Abstract

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Abstract

The use of tertiary amines as surrogates for secondary amines has prominent advantages in terms of stabilization and ease of handling. A Ni-catalyzed transamidation of N-acylsaccharins with tertiary aromatic amines is reported. By using tert-butyl hydroperoxide as the terminal oxidant, this reaction permits selective cleavage of the C(sp³)–N bonds of unsymmetrical tertiary aromatic amines depending on the sizes of the alkyl substituents.

Key words

transamidation - nickel catalysis - amides - tertiary amines - C–N bond cleavage

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References

References and Notes

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