Water-promoted ortho-selective monohydroxymethylation of phenols in the NaBO2 system.
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.
School of Marine Science and Technology, Harbin Institute of Technology at Weihai, Shandong 264209, China. lihuijing@iccas.ac.cn ycwu@iccas.ac.cn.
Hui-Jing
HJ
Li
Ying-Ying
YY
Wu
Qin-Xi
QX
Wu
Rui
R
Wang
Chun-Yang
CY
Dai
Zhi-Lun
ZL
Shen
Cheng-Long
CL
Xie
Yan-Chao
YC
Wu
D001881:Borates / Q000737:chemistry*; D005557:Formaldehyde / Q000737:chemistry; D008745:Methylation; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D001881:Borates; D010636:Phenols; D014867:Water; D005557:Formaldehyde