Download PDF
Synthesis 2014; 46(15): 2045-2050
DOI: 10.1055/s-0033-1338628
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Access to Isoindolinone Derivatives by Palladium-Catalyzed C–H Activation and Isocyanide Insertion by Using Molecular Oxygen as the Sole Oxidant

Dongqi Wang
a   Institute of Chemistry and Biomedical Sciences, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, P. R. of China   Email: yongqian@nju.edu.cn   Email: weiwei@nju.edu.cn
,
Sheng Cai
a   Institute of Chemistry and Biomedical Sciences, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, P. R. of China   Email: yongqian@nju.edu.cn   Email: weiwei@nju.edu.cn
,
Rong Ben
a   Institute of Chemistry and Biomedical Sciences, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, P. R. of China   Email: yongqian@nju.edu.cn   Email: weiwei@nju.edu.cn
,
Yang Zhou
a   Institute of Chemistry and Biomedical Sciences, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, P. R. of China   Email: yongqian@nju.edu.cn   Email: weiwei@nju.edu.cn
,
Xingwei Li
b   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China
,
Jing Zhao
a   Institute of Chemistry and Biomedical Sciences, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, P. R. of China   Email: yongqian@nju.edu.cn   Email: weiwei@nju.edu.cn
c   Shenzhen Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China
,
Wei Wei*
a   Institute of Chemistry and Biomedical Sciences, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, P. R. of China   Email: yongqian@nju.edu.cn   Email: weiwei@nju.edu.cn
,
Yong Qian*
a   Institute of Chemistry and Biomedical Sciences, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, P. R. of China   Email: yongqian@nju.edu.cn   Email: weiwei@nju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 13 January 2014

Accepted after revision: 04 April 2014

Publication Date:
20 May 2014 (online)

    Permissions and Reprints All articles of this category


Abstract

We report a straightforward, aerobic, palladium-catalyzed C–H activation, followed by isocyanide insertion to synthesize isoindolinone derivatives. This transformation is an efficient and step-economic strategy using oxygen as the sole oxidant. We anticipate that this work will inspire in-depth studies as well as versatile applications in various related fields.

Key words

palladium-catalyzed - C–H activation - isocyanide insertion - isoindolinone - oxygen - heterocycles

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
  • Supporting Information
 

  • References

  • 1 These authors contributed equally to this work.
    • 2a Chen X, Engle KM, Wang D.-HYu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
      CrossrefPubMed
    • 2b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
    • 2c Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
  • 3 Brennführer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
    CrossrefPubMed
    • 4a Vlaar T, Maes BU. W, Ruijter E, Orru RV. A. Angew. Chem. Int. Ed. 2013; 52: 7084
      Crossref
    • 4b Lang S. Chem. Soc. Rev. 2013; 42: 4867
      Crossref
    • 4c Qiu G, Ding Q, Wu J. Chem. Soc. Rev. 2013; 42: 5257
      Crossref
  • 5 Curran DP, Du W. Org. Lett. 2002; 4: 3215
    Crossref
  • 6 Tobisu M, Imoto S, Ito S, Chatani N. J. Org. Chem. 2010; 75: 4835
    Crossref
  • 7 Wang Y, Wang H, Peng J, Zhu Q. Org. Lett. 2011; 13: 4604
    CrossrefPubMed
  • 8 Wang Y, Zhu Q. Adv. Synth. Catal. 2012; 354: 1902
    Crossref
  • 9 Peng J, Liu L, Hu Z, Huang J, Zhu Q. Chem. Commun. 2012; 48: 3772
    Crossref
  • 10 Hu Z, Liang D, Zhao J, Huang J, Zhu Q. Chem. Commun. 2012; 48: 7371
    CrossrefPubMed
  • 11 Peng J, Zhao J, Hu Z, Liang D, Huang J, Zhu Q. Org. Lett. 2012; 14: 4966
    Crossref
  • 12 Xu S, Huang X, Hong X, Xu B. Org. Lett. 2012; 14: 4614
    CrossrefPubMed
    • 13a Chen M, He M, Zhou X, Huang L, Ruan Y, Huang P. Tetrahedron 2005; 61: 1335
      Crossref
    • 13b Stuk TL, Assink BK, Bates RC, Erdman DT, Fedij V, Jennings SM, Lassig JA, Smith RJ, Smith TL. Org. Process Res. Dev. 2003; 7: 851
      Crossref
    • 13c Belliotti TR, Brink WA, Kesten SR, Rubin JR, Wustrow DJ, Zoski KT, Whetzel SZ, Corbin AE, Pugsley TA, Heffner TG, Wise LD. Bioorg. Med. Chem. Lett. 1998; 8: 1499
      Crossref
  • 14 Tyagi V, Khan S, Chauhan PM. S. Synlett 2013; 24: 645
    Article in Thieme Connect
  • 15 Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010; 132: 6908
    CrossrefPubMed
  • 16 Simmons EM, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 3066
    Crossref