Synthesis 2020; 52(05): 763-768
DOI: 10.1055/s-0039-1691528
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Oxidative Dearomatization of Indoles with Aromatic Ketones: Rapid Access to 2,2-Disubstituted Indolin-3-ones

Jiarun Liu
,
Jiancheng Huang
,
Kuiyong Jia
,
Tianxing Du
,
Changyin Zhao
,
Rongxiu Zhu
School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   eMail: rxzhu@sdu.edu.cn   eMail: 201990000024@sdu.edu.cn
,
Xigong Liu
› Institutsangaben
This work was financially supported by the National Natural Science Foundation of China (No. 21801093) and the Natural Science Foundation of Shandong Province (Nos. ZR2017BB006, JQ201721).
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Publikationsverlauf

Received: 16. Oktober 2019

Accepted after revision: 16. November 2019

Publikationsdatum:
28. November 2019 (online)


§ These authors contributed equally to this work

Abstract

A metal-free oxidative dearomatization of indoles with aromatic ketones mediated by TEMPO oxoammonium salt is described. The dearomatization proceeds smoothly and displays a broad substrate scope with respect to both indoles and aromatic ketones in the presence of H2SO4, affording the corresponding 2,2-disubstituted indolin-3-ones in good yields.

Supporting Information