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镍催化的芳基硼酸偕二氟炔丙基化反应
其他题名Nickel-Catalyzed Cross-Coupling of gem-Difluoropropargyl Bromide with Aryl Boronic Acids
肖玉兰; 潘强; 张新刚
2015
发表期刊化学学报
卷号73期号:5页码:383-387
其他摘要The gem-difluoropropargylated arenes play an important role in life and material sciences owning to the unique properties of the difluoromethylene group (CF2). The traditional method to access such a kind of fluorinated structure relies on conversion of carbonyl group with aminosulfurtrifluorides, such as DAST and Deoxofluor. However, these reactions suffer from the use of expensive and toxic fluorinated reagents and the important functional group incompatibility. Hence, it is highly desirable to develop new and efficient strategies and methods to prepare gem-difluoropropargylated arenes. As part of our ongoing interest in transition-metal-catalyzed difluoroalkylation reactions, herein, we report a nickel-catalyzed cross-coupling of gem-difluoropropargyl bromide with aryl boronic acids. The reaction uses low-cost Ni-catalyst and proceeds under mild reaction conditions with high efficiency and good functional group compatibility. It is also possible for gram-scale reaction and late stage gem-difluoropropargylation of bioactive natural product, thus providing a facile route for application in drug discovery and development. A representative procedure for nickel-catalyzed cross-coupling of gem-difluoropropargyl bromide with aryl boronic acids is as following: Phenylboronic acid 1a (1.5 equiv.), Ni(NO3)(2)center dot 6H(2)O or NiCl2 center dot dppe (2.5 mol%), bpy (2.5 mol%), and K2CO3 (2.0 equiv.) were subsequently added to a 25 mL of Schlenck tube. The resulting mixture was then evacuated and backfilled with Ar (3 times). gem-Difluoropropargyl bromide 2 (0.6 mmol, 1.0 equiv.) and 1,4-dioxane (4 mL) were then added. The Schlenck tube was screw capped and put into a preheated oil bath (80 degrees C). After stirring for 24 h, the reaction mixture was cooled to room temperature. The yield was determined by F-19 NMR before working up. If necessary, the reaction mixture was diluted with EtOAc and filtered with a pad of cellite. The filtrate was concentrated, and the residue was purified with silica gel chromatography (100% Petroleum ether) to give product 3a.
文章类型论文
学科领域氟化学
DOI10.6023/A15010042
URL查看原文
收录类别SCI
语种中文
WOS记录号WOS:000357389800001
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文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/39732
专题中科院有机氟化学重点实验室
通讯作者张新刚
作者单位中科院上海有机化学研究所, 有机氟化学重点实验室
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肖玉兰,潘强,张新刚. 镍催化的芳基硼酸偕二氟炔丙基化反应[J]. 化学学报,2015,73(5):383-387.
APA 肖玉兰,潘强,&张新刚.(2015).镍催化的芳基硼酸偕二氟炔丙基化反应.化学学报,73(5),383-387.
MLA 肖玉兰,et al."镍催化的芳基硼酸偕二氟炔丙基化反应".化学学报 73.5(2015):383-387.
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