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Synthesis 2019; 51(18): 3477-3484
DOI: 10.1055/s-0037-1611850
paper
© Georg Thieme Verlag Stuttgart · New York

Preparation of 2-(3-Methyleneindolin-2-yl)phenols via Sodium Hydride Promoted C–C/C–O Bond Cleavage

Feng-Ping Liu ◊
a   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China   Email: moeastlight@mailbox.gxnu.edu.cn
,
Hong-Ping Zhao ◊
a   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China   Email: moeastlight@mailbox.gxnu.edu.cn
,
Shuang Tan
a   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China   Email: moeastlight@mailbox.gxnu.edu.cn
,
Xiuqiang Lu
b   Fuqing Branch of Fujian Normal University, Fuzhou, Fujian 350300, P. R. of China
,
Dong-Liang Mo  *
a   State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, P. R. of China   Email: moeastlight@mailbox.gxnu.edu.cn
› Author AffiliationsFinancial support from the National Natural Science Foundation of China (21562005, 51503037), the Natural Science Foundation of Guangxi Province (2016GXNSFFA380005), the Overseas 100 Talents Program of Guangxi Higher Education, and the One Thousand Young and Middle-Aged College and University Backbone Teachers Cultivation Program of Guangxi is greatly appreciated.
Further Information

Publication History

Received: 04 April 2019

Accepted after revision: 13 May 2019

Publication Date:
12 June 2019 (online)

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◊ F.-P. Liu and H.-P. Zhao contributed equally to this work.

Abstract

A variety of 2-(3-methyleneindolin-2-yl)phenols were prepared in good to excellent yields through a NaH-promoted C–C/C–O bond cleavage of fused indolines under mild and simple conditions. Mechanistic studies showed that NaH serves as a nucleophile, attacking the aldehyde group of indoline, which is followed by tandem C–C/C–O bond cleavage to afford the desired products. A representative 2-(3-methyleneindolin-2-yl)phenol was easily prepared on a gram scale.

Key words

cascade reaction - C–C/C–O bond cleavage - indolines - phenols - sodium hydride

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611850.
  • Supporting Information
 

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