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)


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.

Supporting Information

 
  • References and Notes


    • For some selected examples, see:
    • 1a Singhand GS, Desta ZY. Chem. Rev. 2012; 112: 6104
    • 1b Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
    • 1c Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165
    • 1d Trost BM, Brennan MK. Synthesis 2009; 3003
    • 1e Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Tuntland T, Zhang K, Karanewsky D, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2109
    • 1f Kitamura H, Kato A, Esaki T. Eur. J. Pharmacol. 2001; 418: 225

      For some selected examples, see:
    • 3a Jia Y.-X, Kndig EP. Angew. Chem. Int. Ed. 2009; 48: 1636
    • 3b Wu T, Mu X, Liu G. Angew. Chem. Int. Ed. 2011; 50: 12578
    • 3c Broggini G, Barbera V, Beccalli EM, Borsini E, Galli S, Lanza G, Zecchi G. Adv. Synth. Catal. 2012; 354: 159
    • 3d Perry A, Taylor RJ. K. Chem. Commun. 2009; 3249
    • 3e An G, Zhou W, Zhang G, Sun H, Han J, Pan Y. Org. Lett. 2010; 12: 4

      For the difunctionalization of alkenes leading to oxindoles through a radical process, see:
    • 4a Wei WT, Zhou MB, Fan JH, Liu W, Song RJ, Liu Y, Hu M, Xie P, Li J.-H. Angew. Chem. Int. Ed. 2013; 52: 3638
    • 4b Li YM, Sun M, Wang HL, Tian Q.-P, Yang SD. Angew. Chem. Int. Ed. 2013; 52: 3972
    • 4c Xie J, Xu P, Li H, Xue Q, Jin H, Cheng Y, Zhu C. Chem. Commun. 2013; 49: 5672
    • 4d Matcha K, Narayan R, Antonchick AP. Angew. Chem. Int. Ed. 2013; 52: 7985
    • 4e Zhou MB, Song RJ, Ouyang XH, Liu Y, Wei WT, Deng G.-B, Li JH. Chem. Sci. 2013; 4: 2690
    • 4f Li XQ, Xu XS, Hu P, Xiao XQ, Zhou C. J. Org. Chem. 2013; 78: 7343
    • 4g Li Y.-M, Wei XH, Li XA, Yang SD. Chem. Commun. 2013; 49: 11701
    • 4h Majumdar KC, Karunakar GV, Sinha B. Synthesis 2012; 44: 2475
    • 4i Zhang J.-L, Liu Y, Song R.-J, Jiang G.-F, Li J.-H. Synlett 2014; 25: 1031
    • 5a Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
    • 5b Zhou B, Hou W, Yang Y, Feng H, Li YC. Org. Lett. 2014; 16: 1322
    • 5c Vaddula BR, Saha A, Leazer J, Varma RS. Green Chem. 2012; 14: 2133
    • 5d Kang SK, Yoon SK, Kim YM. Org. Lett. 2001; 3: 2697
    • 5e Jalalian N, Ishikawa EE, Silva LF, Olofsson B. Org. Lett. 2011; 13: 1552
    • 5f Petersen TB, Khan R, Olofsson B. Org. Lett. 2011; 13: 3462
    • 5g Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
    • 5h Kraszkiewicz L, Skulski L. Synthesis 2008; 2373
    • 5i Xu J, Zhang PB, Gao YZ, Chen YY, Tang G, Zhao YF. J. Org. Chem. 2013; 78: 8176
    • 5j Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
    • 5k Allen AE, MacMillan DW. C. J. Am. Chem. Soc. 2011; 133: 4260
    • 5l Liu YX, Xue D, Wang JD, Zhao CJ, Zou QZ, Wang C, Xiao J. Synlett 2013; 24: 507
    • 5m During the preparation of our manuscript, similar research was reported: Zhou B, Hou W, Yang Y, Feng H, Li YC. Org. Lett. 2014; 16: 1322
  • 6 Phipps RJ, Gaunt MJ. Science 2009; 323: 1593
    • 7a Walkinshaw AJ, Xu W, Suero MG, Gaunt MJ. J. Am. Chem. Soc. 2013; 135: 12532
    • 7b Suero MG, Bayle ED, Collins BS. L, Gaunt MJ. J. Am. Chem. Soc. 2013; 135: 5332
  • 8 Cahard E, Bremeyer N, Gaunt MJ. Angew. Chem. Int. Ed. 2013; 52: 9284
  • 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.