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Synlett 2014; 25(14): 2009-2012
DOI: 10.1055/s-0034-1378354
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Oxidative Electrophilic Carbofunctionalization of Acrylamides for the Synthesis of Oxindoles

Xueqin Li
a   Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Fax: +86(592)2185780   eMail: t12g21@xmu.edu.cn
,
Jian Xu
a   Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Fax: +86(592)2185780   eMail: t12g21@xmu.edu.cn
,
Pengbo Zhang
a   Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Fax: +86(592)2185780   eMail: t12g21@xmu.edu.cn
,
Yuzhen Gao
a   Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Fax: +86(592)2185780   eMail: t12g21@xmu.edu.cn
,
Ju Wu
a   Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Fax: +86(592)2185780   eMail: t12g21@xmu.edu.cn
,
Guo Tang*
a   Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Fax: +86(592)2185780   eMail: t12g21@xmu.edu.cn
,
Yufen Zhao
a   Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. of China   Fax: +86(592)2185780   eMail: t12g21@xmu.edu.cn
b   Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
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Publikationsverlauf

Received: 05. April 2014

Accepted after revision: 27. Mai 2014

Publikationsdatum:
28. Juli 2014 (online)

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Abstract

A novel and efficient copper-catalyzed tandem oxidative cyclization of arylacrylamides with diaryliodonium salts is reported. This reaction provides a novel approach for the synthesis of oxindoles and various functional groups were well tolerated.

Key words

copper-catalyzed - acrylamides - diphenyliodonium ­triflate - oxindoles - electrophilic arylation

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
  • Supporting Information
 

  • References and Notes


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  • 10 Typical Procedure: An oven-dried 10-mL Schlenk tube containing CuCl (4.5 mg, 15 mol%), N-arylacrylamide 1a (90.3 mg, 0.3 mmol), and diphenyliodonium triflate (2a; 154.8 mg, 0.36 mmol) was evacuated and purged with nitrogen three times. DTBP (68.8 mg, 0.36 mmol) in freshly distilled CH2Cl2 (2.0 mL) was added to the system at r.t. The reaction mixture was heated with stirring at 60 °C for 24 h. The reaction mixture was allowed to cool to ambient temperature, and then transferred to a round-bottom flask. Silica gel (3.0 g) was added, and the solvent was removed under reduced pressure to afford a free-flowing powder. This powder was then dry-loaded onto a silica gel column and purified by flash chromatography using petroleum ether–EtOAc (20:1) as the eluent to give the product 3a. Yield: 75 mg (81%). MS (ESI): m/z = 274.0 [M + Na]+. 1H NMR (400 MHz, CDCl3): δ = 7.03–7.18 (m, 6 H), 6.83–6.85 (m, 2 H), 6.62 (d, J = 7.7 Hz, 1 H), 3.12 (d, J = 13.0 Hz, 1 H), 3.01 (d, J = 13.0 Hz, 1 H), 2.98 (s, 3 H), 1.47 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 179.9, 142.9, 136.0, 132.9, 129.7, 127.6, 126.3, 123.2, 121.9, 107.6, 50.0, 44.4, 26.7, 22.6.