Chemoselective epoxidation of electron-deficient olefins with molecular oxygen via conjugated olefins epoxidation and BHT hydroxylation  

作　　者：Jia Nie Huanfeng Jiang Chuanle Zhu 

机构地区：[1]School of Chemistry and Chemical Engineering,Key Lab of Functional Molecular Engineering of Guangdong Province,South China University of Technology,Guangzhou 510640,China [2]Guangdong Provincial Key Laboratory of Technique and Equipment for Macromolecular Advanced Manufacturing,South China University of Technology,Guangzhou 510640,China

出　　处：《Science China Chemistry》2024年第9期3012-3018,共7页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(22271097);the Guangdong Basic and Applied Basic Research Foundation(2022A1515240017)。

摘　　要：The chemoselective epoxidation of electron-deficient olefins in the presence of electron-rich alkene moieties is reported.This chemoselective epoxidation strategy undergoes a conjugated olefin epoxidation and BHT hydroxylation process to give various useful oxiranes in high yields,especially for the 2-substituted 2-trifluoromethyloxiranes.Importantly,this protocol features mild conditions,is transition-metal free,operationally simple,and gram-scalable,and tolerates diverse functional groups.Drug candidate HSD-16 is synthesized smoothly by this protocol.Mechanism studies indicate molecular oxygen is the terminal oxidant and the O-source of the oxiranes.

关 键 词：CHEMOSELECTIVE EPOXIDATION ALKENE fluorine molecular oxygen 

分 类 号：O621.251[理学—有机化学]