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

Ruthenium-Catalyzed Oxidative Dearomatization of N-Boc Indoles

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
› Author Affiliations
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).


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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