Magnetic Copper Ferrite Nanoparticles: An Inexpensive, Efficient, Recyclable Catalyst for the Synthesis of Substituted Benzoxazoles via Ullmann-Type Coupling under Ligand-Free Conditions

Daoshan Yang; Xiao Zhu; Wei Wei; Min Jiang; Ning Zhang; Dandan Ren; Jinmao You; Hua Wang

doi:10.1055/s-0033-1340599

Synlett, Table of Contents

Synlett 2014; 25(5): 729-735
DOI: 10.1055/s-0033-1340599

letter

Magnetic Copper Ferrite Nanoparticles: An Inexpensive, Efficient, Recyclable Catalyst for the Synthesis of Substituted Benzoxazoles via Ullmann-Type Coupling under Ligand-Free Conditions

Daoshan Yang

^aShandong Province Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China Fax: +86(537)4458306 Email: huawang_qfnu@126.com

,

Xiao Zhu

^aShandong Province Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China Fax: +86(537)4458306 Email: huawang_qfnu@126.com

,

Wei Wei

^aShandong Province Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China Fax: +86(537)4458306 Email: huawang_qfnu@126.com

,

Min Jiang

^bBeijing Key Laboratory for Analytical Methods and Instrumentation, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China

,

Ning Zhang

^aShandong Province Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China Fax: +86(537)4458306 Email: huawang_qfnu@126.com

,

Dandan Ren

^aShandong Province Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China Fax: +86(537)4458306 Email: huawang_qfnu@126.com

,

Jinmao You

^aShandong Province Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China Fax: +86(537)4458306 Email: huawang_qfnu@126.com

^cKey Laboratory of Adaptation and Evolution of Plateau Biota, Northwest Institute of Plateau Biology, Chinese Academy of Science, Xining 810008, P. R. of China

,

Hua Wang*

^aShandong Province Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, P. R. of China Fax: +86(537)4458306 Email: huawang_qfnu@126.com

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Abstract

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Abstract

A new sustainable strategy for the synthesis of benzoxazoles from substituted N-(2-halophenyl)benzamides was developed in which inexpensive, readily available, air-stable, recyclable copper(II) ferrite serves as a nanocatalyst. The nanocatalyst can be completely recovered with an external magnet and can be used seven times without significant loss of catalytic activity.

Key words

nanostructures - catalysts - copper - iron - heterocycles - cyclizations - coupling

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References

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19 2-Phenyl-1,3-benzoxazoles 2; General Procedure A 25 mL Schlenk tube equipped with a magnetic stirring bar was charged with CuFe₂O₄ nanoparticles (0.05 mmol, 12 mg), benzamide 1 (0.5 mmol), and K₂CO₃ (1.0 mmol, 139 mg). The tube was evacuated twice and backfilled with N₂. DMSO (1.5 mL) was added under N₂, the tube was sealed, and then the mixture was stirred at 90–120 °C for 24 h. When the reaction was complete, the solution was cooled to r.t. and concentrated in a rotary evaporator. The residue was purified by column chromatography (silica gel, PE–EtOAc). 2-Phenyl-1,3-benzoxazole (2a) Eluent: PE–EtOAc (20:1); white solid; yield: 94 mg (96%); mp 101–102 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.29 (d, J = 7.6 Hz, 2 H), 7.80 (d, J = 3.2 Hz, 1 H), 7.61 (d, J = 3.6 Hz, 1 H), 7.62–7.54 (m, 3 H), 7.38 (d, J = 6.0 Hz, 2 H). ¹³C NMR (200 MHz, CDCl₃): δ = 163.1, 150.8, 142.1, 131.5, 128.9, 127.6, 127.2, 125.1, 124.6, 120.0, 110.6. ESI-MS: m/z = 196.3 [M + H]⁺. 6-Chloro-2-phenyl-1,3-benzoxazole (2j) Eluent: PE–EtOAc (20:1); white solid; yield: 109 mg (95%); mp 107–108 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.26 (d, J = 6.0 Hz, 2 H), 7.71–7.69 (d, J = 8.4 Hz, 1 H), 7.62–7.53 (m, 4 H), 7.36 (d, J = 8.4 Hz, 1 H). ¹³C NMR (200 MHz, CDCl₃): δ = 163.7, 151.0, 141.0, 131.8, 130.7, 129.0, 127.7, 126.7, 125.3, 120.5, 111.3. ESI-MS: m/z = 230.5 [M + H]⁺.

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