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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‡
a   College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Lingyun Yang‡
a   College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Jiasi Tao
a   College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Weijie Yu
a   College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Tao Wang∗
a   College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
b   National 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  ∗
a   College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
b   National Research Center for Carbohydrate Synthesis, Jiangxi Province’s Key Laboratory of Chemical Biology, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
› InstitutsangabenWe gratefully acknowledge financial support from the National Natural Science Foundation of China (21762025, 21562026) and the Key Projects of Natural Science Foundation of Jiangxi Province (20192ACBL20026).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1517-5895.
  • Supporting Information


Publikationsverlauf

Eingereicht: 30. April 2021

Angenommen nach Revision: 25. Mai 2021

Accepted Manuscript online:
25. Mai 2021

Artikel online veröffentlicht:
09. Juni 2021

© 2021. Thieme. All rights reserved

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