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光氧化还原催化六氟丙酮水合物脱氧实现烯烃的羟基多氟烷基化
作者:小柯机器人 发布时间:2022/9/21 14:37:37

中南大学阳华团队报道了光氧化还原催化六氟丙酮水合物的脱氧实现烯烃的羟基多氟烷基化。相关研究成果于2022年9月16日发表于国际顶尖学术期刊《德国应用化学》。

该文建立了一种前所未有的光氧化还原催化膦介导的六氟丙酮水合物的脱氧反应,以实现缺电子烯烃的羟基聚氟烷基化。使用现成的六氟丙酮水合物代替有毒的气态六氟丙酮,可以方便地获得一系列双(三氟甲基)甲醇。可耐受一系列缺电子烯烃,从而以中到高收率获得相应的氢羟聚氟烷基化产物。该合成策略的显著特点包括操作简单、反应条件温和、区域选择性好和官能团耐受性广。

该策略的成功依赖于醛/酮-宝石二醇内禀平衡的巧妙利用,它为具有综合挑战性的聚氟烷基化支架的组装提供了一种创新的开壳方法。

附:英文原文

Title: Photoredox-Catalyzed Deoxygenation of Hexafluoroacetone Hydrate Enables Hydroxypolyfluoroalkylation of Alkenes

Author: Zhen-Zhen Xie, Yu Zheng, Chu-Ping Yuan, Jian-Ping Guan, Zhi-Peng Ye, Jun-An Xiao, Hao-Yue Xiang, Kai Chen, Xiao-Qing Chen, Hua Yang

Issue&Volume: 2022-09-16

Abstract: An unprecedented photoredox-catalyzed phosphine-mediated deoxygenation of hexafluoroacetone hydrate was established to accomplish the hydroxylpolyfluoroalkylation of electron-deficient alkenes. A range of bis(trifluoromethyl)carbinols were facilely accessed by using readily available hexafluoroacetone hydrate, instead of toxic gaseous hexafluoroacetone. A range of electron-deficient alkenes are tolerated, giving the corresponding hydro-hydroxylpolyfluoroalkylated products in moderate to high yields. Remarkable features of this synthetic strategy include operational simplicity, mild reaction conditions, excellent regioselectivity, and broad functional group tolerance. The success of this strategy relies on the delicate utilization of aldehyde/ketone— gem  -diol intrinsic equilibrium, which offers an innovated open-shell pathway for the assembly of synthetically challenging polyfluoroalkylated scaffolds.

DOI: 10.1002/anie.202211035

Source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202211035

期刊信息

Angewandte Chemie:《德国应用化学》,创刊于1887年。隶属于德国化学会,最新IF:12.959
官方网址:https://onlinelibrary.wiley.com/journal/15213773
投稿链接:https://www.editorialmanager.com/anie/default.aspx