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Published on: August 17, 2019
Water-promoted ortho-selective monohydroxymethylation of phenols in the NaBO2 system
Hui-Jing Li1, Ying-Ying Wu, Qin-Xi Wu
1School of Marine Science and Technology, Harbin Institute of Technology at Weihai, Shandong 264209, China. lihuijing@iccas.ac.cn ycwu@iccas.ac.cn.
Abstract:
Water-promoted ortho-selective monohydroxymethylation of phenols in the NaBO2 system generates salicyl alcohols in 65-97% yields. A remarkable rate-enhancement by water was observed, and NaBO2 appeared to serve the dual role of a suitable base and an efficient chelating reagent. This protocol possesses many advantages such as short reaction times, expanded substrate scope, and high mono- and regio-selectivities. The experimental results were explained by the calculations based on local ionisation energy minima, leading to a possible reaction mechanism.
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