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Synlett 2012; 23(16): 2393-2396
DOI: 10.1055/s-0032-1317097
letter
© Georg Thieme Verlag Stuttgart · New York

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

Yan Zong
a   Jiangsu 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
a   Jiangsu 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*
a   Jiangsu 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
b   Key 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*
a   Jiangsu 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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Publikationsverlauf

Received: 13. Juni 2012

Accepted after revision: 24. Juli 2012

Publikationsdatum:
31. August 2012 (online)

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Erratum zu diesem Artikel:

Synthesis of Biaryl Derivatives via a Magnetic Pd-NPs-Catalyzed One-Pot ­Diazotization–Cross-Coupling ReactionSynlett 2012; 23(20): 3001-3001
DOI: 10.1055/s-0032-1317941

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

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

  • 7 Hu JF, Wang YP, Han M, Zhou YM, Sun PP, Jiang XQ. Catal. Sci. Tech. 2012; in press; DOI: 10.1039/ C2CY20263H
  • 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