Copper-Mediated Fluoroalkylation of Aryl Bromides and Chlorides Enabled by Directing Groups.
Copper-Mediated Fluoroalkylation of Aryl Bromides and Chlorides Enabled by Directing Groups.
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DOI：
10.1021/acs.organomet.3c00066
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发表时间：
2023-03
期刊：
影响因子：
2.8
通讯作者：
Jonathan R. Hall;Isaac M Blythe;Liam S. Sharninghausen;M. Sanford
中科院分区：
文献类型：
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作者：
Jonathan R. Hall;Isaac M Blythe;Liam S. Sharninghausen;M. Sanford
本文报道了N-杂环卡宾铜(I)氟烷基配合物与含邻位导向基团的芳基卤化物的反应。吡啶、吡唑、恶唑啉、亚胺和酯类导向基团能显著提高芳基溴化物和氯化物与CuI-氟烷基络合物(IPR=1，3-bis(2，6-diisopropylphenyl)imidazol-2-ylidene；氟烷基=二氟甲基和五氟乙基)的反应活性，生成芳基-氟烷基偶联产物。这种方法被用来实现铜催化的一系列芳基溴底物的直接氟烷基化反应。
This report describes the reactions between N-heterocyclic carbene copper(I) fluoroalkyl complexes and aryl halides bearing ortho-directing groups. Pyridine, pyrazole, oxazoline, imine, and ester directing groups are shown to dramatically enhance the reactivity of aryl bromides and chlorides with (IPr)CuI-fluoroalkyl complexes (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; fluoroalkyl = difluoromethyl and pentafluoroethyl) to afford aryl-fluoroalkyl coupling products. This approach is leveraged to achieve the Cu-catalyzed directed fluoroalkylation of a series of aryl bromide substrates.