Highly Efficient Mechanochemical N-Arylation of Amino Alcohols and Diamines with Cu0 Powder

Katia Martina; Laura Rinaldi; Francesca Baricco; Luisa Boffa; Giancarlo Cravotto

doi:10.1055/s-0035-1560173

Synlett, Table of Contents

Synlett 2015; 26(20): 2789-2794
DOI: 10.1055/s-0035-1560173

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Highly Efficient Mechanochemical N-Arylation of Amino Alcohols and Diamines with Cu⁰ Powder

Katia Martina

Dipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin, Italy Email: giancarlo.cravotto@unito.it

,

Laura Rinaldi

Dipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin, Italy Email: giancarlo.cravotto@unito.it

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Francesca Baricco

Dipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin, Italy Email: giancarlo.cravotto@unito.it

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Luisa Boffa

Dipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin, Italy Email: giancarlo.cravotto@unito.it

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Giancarlo Cravotto*

Dipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin, Italy Email: giancarlo.cravotto@unito.it

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Abstract

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Abstract

Cu⁰-catalysed arylations have rightly acquired great importance over the last decade. This paper reports the N-arylation of amino alcohols and diamines with iodobenzene derivatives in a planetary ball mill and an investigation into the procedure. This newly developed solvent-free protocol is fast, efficient and occurs under the mechanochemical activation of metallic copper powder. It does not require additional ligands and gives excellent yields. This paper aims to broaden the scope of mechanochemical Cu⁰-activation and so a new one-pot, two-step synthesis that combines CuAAC and N-arylation has been successfully performed and reported herein.

Key words

N-arylation - mechanochemistry - Cu⁰-catalysed cross-coupling - solvent-free reaction - amino alcohols

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References

References and Notes

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29 General Procedure for Cu⁰-Catalysed N-Arylation of Amino Alcohols or Ethylendiamine with Iodobenzenes in Ball Mill: The milling jar (50 mL; stainless steel) were equipped with 1500 milling balls (d = 2 mm, stainless steel) and 48 medium balls (d = 5 mm, stainless steel). Afterwards basic Al₂O₃ 90 active (1 g), and KOH (3.7 mmol) were added and milled for 10 min at 450 rpm. After that the aryl iodide (1 mmol), the amino alcohol (3 mmol) or ethylendiamine (10 mmol) and Cu⁰ powder (1 mmol, 63 mg) were added in the given order. Milling was accomplished at 650 rpm for 30 min. After cooling of the milling jar to r.t., the crude products were washed from Al₂O₃ on Büchner funnel with a sintered glass disc using ethyl acetate. The solvent was evaporated in vacuum, the crude products were dried and analysed by GC–MS. The mixture was purified by flash chromatography on silica gel (hexane–EtOAc) to afford the desired product. The pure products were analysed by ¹H NMR, ¹³C NMR spectroscopy and MALDI–TOF mass spectrometry after dissolution in an appropriate solvent.
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34 3-(N-Methyl-4-methoxyphenylamino)propane-1,2-diol (3n): yellowish amorphous solid (32%). ¹H NMR (300 MHz, CDCl₃): δ = 6.85 (m, 4 H), 3.95 (m, 1 H), 3.76 (m, 4 H), 3.52–3.58 (dd, J = 6.0 Hz, 1 H), 3.26–3.29 (m, 1 H), 3.16 (m, 1 H), 2.87 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 153.28, 144.64, 116.69, 114.57, 68.89, 64.20, 57.78, 55.62, 40.51. MS (MALDI–TOF): m/z [M + H]⁺ calcd for C₁₁H₁₇NO₃: 212.1256; found: 212.1264.
35 Triazole derivative 3o: white powder (56%). ¹H NMR (300 MHz, CDCl₃): δ = 7.71 (d, J = 8.4 Hz, 2 H), 7.53 (s, 1 H), 7.34 (d, J = 7.3 Hz, 2 H), 7.17–7.27 (m, 1 H), 6.56 (d, J = 8.5 Hz, 2 H), 5.36 (s, 2 H), 3.11 (br s, 2 H), 2.89 (t, J = 5.7 Hz, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 149.3, 148.3, 131.1, 130.2, 129.2, 128.4, 126.1, 123.1, 119.6, 113.5, 54.5, 46.6, 41.4. MS (MALDI–TOF): m/z [M + H]⁺ calcd for C₁₇H₁₉N₅: 294.1640; found: 294.1644.

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