Synthesis of difluoromethylated benzylborons via rhodium(I)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes
Synthesis of difluoromethylated benzylborons via rhodium(I)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes
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DOI：
10.1016/j.cclet.2020.03.031
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发表时间：
2021-02-12
影响因子：
9.1
通讯作者：
Wang, Honggen
中科院分区：
文献类型：
--
作者：
Cai, Yuanhong;Tan, Donghang;Wang, Honggen
硼化有机氟的合成由于其作为含氟分子模块化结构的合成子的潜在价值而引起了人们的极大兴趣。本文报道了一种铑催化的芳基宝石-二氟烯烃的硼氢化反应，得到了一系列的-二氟甲基化苯硼。使用阳离子铑催化剂和大咬角的二膦配体对反应活性至关重要，因为它提供了良好的区域选择性和减少了不需要的β - f消除。对产品进行了初步衍生，以展示该协议的实用性。(C) 2020中国化学学会、中国医学科学院药物研究所。Elsevier B.V.版权所有。
The synthesis of borylated organofluorines is of great interest due to their potential values as synthons in modular construction of fluorine-containing molecules. Reported herein is a rhodium-catalyzed hydroboration of aryl gem-difluoroalkenes leading to a series of alpha-difluoromethylated benzylborons. The use of cationic rhodium catalyst and a biphosphine ligand with large bite angle was crucial for reactivity by offering good regioselectivity and diminishing the undesired beta-F elimination. Preliminary derivatizations of the products were conducted to showcase the utility of this protocol. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.