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Synthesis 2019; 51(18): 3477-3484
DOI: 10.1055/s-0037-1611850
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
Financial 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)
![](https://www.thieme-connect.de/media/synthesis/201918/lookinside/thumbnails/ss-2019-h0103-op_10-1055_s-0037-1611850-1.jpg)
◊ 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.
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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For selected examples of NaH used as a base, see:
For selected examples of the preparation of indoline scaffolds, see: