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

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

Published:2019-06-12 Issue:18 Volume:51 Page:3477-3484
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Liu Feng-Ping¹,Zhao Hong-Ping¹,Tan Shuang¹,Lu Xiuqiang²,Mo Dong-Liang¹^ORCID

Affiliation:

1. 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

2. Fuqing Branch of Fujian Normal University

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.

Funder

Natural Science Foundation of Guangxi Province

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1611850.pdf

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