Use of functionalized aromatic organozinc reagents in the three-component Mannich-type synthesis of diarylmethylamines

Tetrahedron Letters

Volumn 47, Issue 15, 2006, Pages 2497-2500

  Le Gall, Erwan ^a   Troupel, Michel ^a   Nédélec, Jean Yves ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

Author keywords

Aromatic aldehydes; Aromatic organozinc reagents; Diarylmethylamines; Secondary amines; Three component reaction

Indexed keywords

ALDEHYDE; AMINE; AROMATIC COMPOUND; DIARYLMETHYLAMINE DERIVATIVE; PHENYL GROUP; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MANNICH REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33644883034     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.056     Document Type: Article

References (32)

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29. Owing to the fact that in the original work, organozinc reagents were prepared on a 15 mmol scale and that in this work 30 mmol of the aryl bromide were used, optimization of the original procedure was done: trifluoromethanesulfonic acid was used instead of trifluoroacetic acid and the mixture was kept at room temperature using a water bath after addition of the aryl bromide. These modifications of experimental conditions resulted in the formation of organozinc species in better yields (typically ranging from 80% to 95%) than using the original procedure (+5-10%).
30. In a typical procedure, a dried 100 mL tricol was flushed with argon and charged with acetonitrile (40 mL). Dodecane (0.20 mL, used as internal standard), cobalt bromide (0.66 g, 3 mmol), zinc bromide (0.68 g, 3 mmol), phenyl bromide (0.32 mL, 3 mmol), and zinc dust (6 g, 92 mmol) were added to the solution. Trifluoromethanesulfonic acid (0.20 mL) was added to the mixture under vigorous stirring. After ca. 15 min, the aryl bromide (30 mmol) was added to the solution and as soon as the exothermic reaction had began (ca. 5 min), a water bath at room temperature was used to moderate the temperature of the medium. The reaction time, which was monitored using gas chromatography, did not exceed 30 min in most cases. Coupling method A: The organozinc-containing solution was transferred via a syringe into a flask flushed with argon. Cuprous iodide (6 mmol) was first added under stirring into the solution followed by the addition of the aldehyde (10 mmol) and the amine (10 mmol). The stirring was continued for additional 3 h at room temperature. Coupling method B: A three-necked flask was equipped with a vertical water-cooled condenser and charged with acetonitrile (15 mL). The secondary amine (10 mmol) and the aldehyde (10 mmol) were added into the solvent and the mixture was heated at 70°C. An addition funnel, connected above the condenser, was charged with the organozinc-containing solution. This solution was added dropwise (ca. 2 h) to the pre-heated mixture and stirred for additional 2 h at 70°C. A typical acid-base workup was then applied to crude light brown oils, which were dissolved in diethyl ether. In each case, the diarylmethylamine was separated from by-products as its ammonium sulfate form by adding sulfuric acid then taken-up in dichloromethane in alkaline conditions. After drying over sodium sulfate and evaporation, analytically pure diarylmethylamines (>97% GC) were obtained as pale yellow liquids, which generally soon crystallized.
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32. +: 320.1626, found: 320.1634.