Synthesis 2021; 53(06): 1121-1126
DOI: 10.1055/s-0040-1706539
paper

Ruthenium-Catalyzed Oxidative Dearomatization of N-Boc Indoles

Authors

  • Xia Chen

    a   School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, P. R. of China   Email: zhouxiaoyu20062006@126.com
  • Xiao-Yu Zhou

    a   School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, P. R. of China   Email: zhouxiaoyu20062006@126.com
  • Xiu-Juan Feng

    b   State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China
  • Ming Bao

    b   State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China

This work was supported by the Foundation of Guizhou Educational Committee (Grant No. qianjiaohe KY zi [2019]081), the Natural Science Foundation of Guizhou Province (Grant No. qiankehejichu [2018]1141) and the Natural Science Foundation of Liupanshui City (Grant No. 52020-2018-04-10).


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Abstract

Ruthenium-catalyzed oxidative dearomatization of N-Boc indoles for the synthesis of indolin-3-ones is described. The N-Boc indoles can be transformed into indolin-3-ones in acetonitrile, using RuCl­3·3H2O as catalyst and sodium periodate (1.5 equiv) as oxidant. Further, a possible mechanism has been proposed on the basis of control experiments.

Supporting Information



Publication History

Received: 01 September 2020

Accepted after revision: 18 September 2020

Article published online:
19 October 2020

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