Synthesis of Biaryl Derivatives via a Magnetic Pd-NPs-Catalyzed One-Pot 
Diazotization–Cross-Coupling Reaction

Yan Zong; Jiefeng Hu; Peipei Sun; Xiaoqing Jiang

doi:10.1055/s-0032-1317097

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(16): 2393-2396
DOI: 10.1055/s-0032-1317097

letter

Synthesis of Biaryl Derivatives via a Magnetic Pd-NPs-Catalyzed One-Pot Diazotization–Cross-Coupling Reaction

Yan Zong

^aJiangsu Key Laboratory of Biofunctional Materials, College of Chemistry and Materials Science, College of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210097, P. R. of China, eMail: jiangxiaoqing@njnu.edu.cn

,

Jiefeng Hu

^aJiangsu Key Laboratory of Biofunctional Materials, College of Chemistry and Materials Science, College of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210097, P. R. of China, eMail: jiangxiaoqing@njnu.edu.cn

,

Peipei Sun*

^aJiangsu Key Laboratory of Biofunctional Materials, College of Chemistry and Materials Science, College of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210097, P. R. of China, eMail: jiangxiaoqing@njnu.edu.cn

^bKey Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. of China, Fax: +86(25)85891767 eMail: sunpeipei@njnu.edu.cn

,

Xiaoqing Jiang*

^aJiangsu Key Laboratory of Biofunctional Materials, College of Chemistry and Materials Science, College of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210097, P. R. of China, eMail: jiangxiaoqing@njnu.edu.cn

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Abstract

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Abstract

A magnetic Pd-NPs-catalyzed one-pot diazotization–cross-coupling reaction of anilines and arylboronic acids was developed. Biaryl derivatives were therefore synthesized in good to excellent yields. Through magnetic separation, the catalyst could be recovered and reused for five times. There were several obvious advantages such as broad applicability, high selectivity, simply experimental operation as well as the convenient preparation, high efficiency and reusability of catalyst.

Key words

nanopalladium - catalysis - diazotization - cross-coupling - magnetic separation

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Referenzen

References and Notes

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9 Typical Procedure for the One-Pot Diazotization–Cross-Coupling Reaction To a Schlenk tube (15 mL) initially fitted with arylamine (0.5 mmol) and MeOH (3 mL) at 0 °C were added t-BuONO (0.075 mL, 0.6 mmol) and BF₃·OEt₂ (0.013 mL, 0.1 mmol). The resulting mixture was stirred for 30 min at 0 °C. To the reaction mixture, kept at 0 °C, were sequentially added arylboronic acid (1 mmol), Pd/Fe₃O₄/s-graphene (3.2 mg, 0.5 mol%). The reaction mixture was allowed to reach 60 °C and stirred for 5 h. After completion of the reaction, the catalyst was recovered by magnetic separation. The solution was diluted with H₂O (10 mL) and extracted with EtOAc (3 × 10 mL). The organic layers were combined, dried over anhyd Na₂SO₄, and purified by column chromatography on silica gel with hexane–EtOAc (10:1) as eluent to yield the pure product. The precipitate was further washed sufficiently with MeOH and Et₂O, and the Pd nanoparticles were recovered for the further use. Ethyl biphenyl-4-carboxylate ¹H NMR (400 MHz, CDCl₃): δ = 1.45 (t, J = 7.1 Hz, 3 H), 4.42 (q, J = 7.1 Hz, 2 H), 7.41–7.44 (m, 1 H), 7.48–7.52 (m, 2 H), 7.65–7.70 (m, 4 H), 8.16 (d, J = 7.9 Hz, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 14.3, 60.9, 127.0, 127.2, 128.1, 128.9, 129.2, 130.0, 140.0, 145.5, 166.5. 4-Bromo-4′-methoxybiphenyl ¹H NMR (400 MHz, CDCl₃): δ = 3.86 (s, 3 H), 7.00 (d, J = 7.7 Hz, 2 H), 7.43 (d, J = 7.8 Hz, 2 H), 7.50–7.56 (m, 4 H). ¹³C NMR (100 MHz, CDCl₃): δ = 55.3, 114.3, 120.7, 127.9, 128.3, 131.7, 132.5, 139.7, 159.4

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