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Synlett 2021; 32(16): 1642-1646
DOI: 10.1055/a-1517-5895
DOI: 10.1055/a-1517-5895
cluster
Modern Nickel-Catalyzed Reactions
Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N-Acylsaccharins
We 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).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1517-5895.
- Supporting Information
Publication History
Received: 30 April 2021
Accepted after revision: 25 May 2021
Accepted Manuscript online:
25 May 2021
Article published online:
09 June 2021
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22
N-Methyl-N-phenylbenzamide (3a): Typical Procedure
A 20 mL standard Schlenk tube equipped with a stirrer bar was charged with N-benzoylsaccharin (1a; 51.4 mg, 0.2 mmol, 1.0 equiv) and Ni(OTf)2 (3.6 mg, 0.02 mmol, 0.10 equiv) under N2. TBHP (28.8 μL, 0.3 mmol, 1.5 equiv), N,N-dimethylaniline (2a; 30.4 μL, 0.22 mmol, 1.1 equiv), and anhyd 1,4-dioxane (3.0 mL) were added with vigorous stirring at rt. The mixture was heated at 100 °C in an oil bath for 12 h then cooled to rt. H2O was added and the resulting mixture was poured into a separatory funnel and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and concentrated under a vacuum. The crude product was purified by column chromatography [silica gel, hexane–EtOAc (20:1)] to give a yellow oily liquid; yield: 32.1 mg (76%).
1H NMR (400 MHz, CDCl3): δ = 7.30–7.28 (m, 2 H), 7.20–7.15 (m, 3 H), 7.13–7.06 (m, 3 H), 7.01 (d, J = 7.6 Hz, 2 H), 3.46 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 170.4, 144.7, 135.8, 129.4, 128.9, 128.5, 127.5, 126.7, 126.3, 38.2. HRMS (ESI-TOF): m/z [M + Na]+ calcd for C14H13NNaO: 234.0895; found: 234.0898.
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For selected reviews, see:
For selected examples on C–N bond cleavage of tertiary amines, see: