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Xia XD, Lu LQ, Liu WQ, et al. Visible-Light-Driven Photocatalytic Activation of Inert Sulfur Ylides for 3-Acyl Oxindole Synthesis. Chemistry. 2016;22(25):8432-7doi: 10.1002/chem.201600871.
Xia, X. D., Lu, L. Q., Liu, W. Q., Chen, D. Z., Zheng, Y. H., Wu, L. Z., & Xiao, W. J. (2016). Visible-Light-Driven Photocatalytic Activation of Inert Sulfur Ylides for 3-Acyl Oxindole Synthesis. Chemistry (Weinheim an der Bergstrasse, Germany), 22(25), 8432-7. https://doi.org/10.1002/chem.201600871
Xia, Xu-Dong, et al. "Visible-Light-Driven Photocatalytic Activation of Inert Sulfur Ylides for 3-Acyl Oxindole Synthesis." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,25 (2016): 8432-7. doi: https://doi.org/10.1002/chem.201600871
Xia XD, Lu LQ, Liu WQ, Chen DZ, Zheng YH, Wu LZ, Xiao WJ. Visible-Light-Driven Photocatalytic Activation of Inert Sulfur Ylides for 3-Acyl Oxindole Synthesis. Chemistry. 2016 Jun 13;22(25):8432-7. doi: 10.1002/chem.201600871. Epub 2016 Apr 26. PMID: 27002773.
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Chemistry. 2016 Jun 13;22(25):8432-7. doi: 10.1002/chem.201600871. Epub 2016 Apr 26.

Visible-Light-Driven Photocatalytic Activation of Inert Sulfur Ylides for 3-Acyl Oxindole Synthesis.

Chemistry (Weinheim an der Bergstrasse, Germany)

Xu-Dong Xia, Liang-Qiu Lu, Wen-Qiang Liu, Dong-Zhen Chen, Yu-Han Zheng, Li-Zhu Wu, Wen-Jing Xiao

Affiliations

  1. Key Laboratory of Pesticide & Chemical Biology, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei, 430079, P. R. China.
  2. Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese, Academy of Sciences, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
  3. Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese, Academy of Sciences, Chinese Academy of Sciences, Beijing, 100190, P. R. China. [email protected].
  4. Key Laboratory of Pesticide & Chemical Biology, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei, 430079, P. R. China. [email protected].

PMID: 27002773 DOI: 10.1002/chem.201600871

Abstract

Bicarbonyl-substituted sulfur ylide is a useful, but inert reagent in organic synthesis. Usually, harsh reaction conditions are required for its transformation. For the first time, it was demonstrated that a new, visible-light photoredox catalytic annulation of sulfur ylides under extremely mild conditions, permits the synthesis of oxindole derivatives in high selectivities and efficiencies. The key to its success is the photocatalytic single-electron-transfer (SET) oxidation of the inert amide and acyl-stabilized sulfur ylides to reactive radical cations, which easily proceeds with intramolecular C-H functionalization to give the final products.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: C−H functionalization; oxindoles; photocatalysis; sulfur ylides; visible light

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