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

Feng-Ping Liu; Hong-Ping Zhao; Shuang Tan; Xiuqiang Lu; Dong-Liang Mo

doi:10.1055/s-0037-1611850

Synthesis, Table of Contents

Synthesis 2019; 51(18): 3477-3484
DOI: 10.1055/s-0037-1611850

paper

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

Feng-Ping Liu ◊

^aState 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 ◊

^aState 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

^aState 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

^bFuqing Branch of Fujian Normal University, Fuzhou, Fujian 350300, P. R. of China

,

Dong-Liang Mo *

^aState 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

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Abstract

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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

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References

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10 CCDC 1855985 (2a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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