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Palladium-catalysed electrophilic aromatic C-H fluorination

机译：钯催化亲电C-H氟化

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摘要

Aryl fluorides are widely used in the pharmaceutical and agrochemical industries(1,2), and recent advances have enabled their synthesis through the conversion of various functional groups. However, there is a lack of general methods for direct aromatic carbon-hydrogen (C-H) fluorination(3). Conventional methods require the use of either strong fluorinating reagents, which are often unselective and difficult to handle, such as elemental fluorine, or less reactive reagents that attack only the most activated arenes, which reduces the substrate scope. A method for the direct fluorination of aromatic C-H bonds could facilitate access to fluorinated derivatives of functional molecules that would otherwise be difficult to produce. For example, drug candidates with improved properties, such as increased metabolic stability or better blood-brain-barrier penetration, may become available. Here we describe an approach to catalysis and the resulting development of an undirected, palladium-catalysed method for aromatic C-H fluorination using mild electrophilic fluorinating reagents. The reaction involves a mode of catalysis that is unusual in aromatic C-H functionalization because no organometallic intermediate is formed; instead, a reactive transition-metal-fluoride electrophile is generated catalytically for the fluorination of arenes that do not otherwise react with mild fluorinating reagents. The scope and functional-group tolerance of this reaction could provide access to functional fluorinated molecules in pharmaceutical and agrochemical development that would otherwise not be readily accessible.
机译：芳基氟化物被广泛用于制药和农业化学工业（1,2），并且最近的进展使它们能够通过各种官能团的转化而合成。但是，缺乏直接的芳族碳氢（C-H）氟化的通用方法（3）。常规方法需要使用强氟化试剂，它们通常是非选择性的且难以处理，例如元素氟，或者反应活性较低的试剂，其仅侵蚀最活化的芳烃，这会减小底物范围。用于芳族C-H键的直接氟化的方法可以促进获得否则难以生产的功能分子的氟化衍生物。例如，具有改善的性质，例如增加的代谢稳定性或更好的血脑屏障渗透性的候选药物可能变得可用。在这里，我们描述了一种催化方法以及使用温和的亲电氟化试剂进行无指导的，钯催化的芳族C-H氟化方法的发展。该反应涉及一种催化方式，这在芳族C-H官能化中是不常见的，因为没有形成有机金属中间体。取而代之的是，催化生成反应性过渡金属氟化物亲电试剂，用于氟化芳烃，而芳烃不会与温和的氟化试剂发生反应。该反应的范围和官能团耐受性可提供药物和农用化学开发中功能性氟化分子的通道，否则该分子将不容易获得。

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  • 来源
    《Nature》 |2018年第7693期|511-514|共4页
  • 作者

    Yamamoto Kumiko; Li Jiakun; Garber Jeffrey A. O.; Rolfes Julian D.; Boursalian Gregory B.; Borghs Jannik C.; Genicot Christophe; Jacq Jerome; van Gastel Maurice; Neese Frank; Ritter Tobias;

  • 作者单位

    Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany|Harvard Univ, Dept Chem & Chem Biol, 12 Oxford St, Cambridge, MA 02138 USA;

    Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany;

    Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany|Harvard Univ, Dept Chem & Chem Biol, 12 Oxford St, Cambridge, MA 02138 USA;

    Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany|Harvard Univ, Dept Chem & Chem Biol, 12 Oxford St, Cambridge, MA 02138 USA;

    Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany|Harvard Univ, Dept Chem & Chem Biol, 12 Oxford St, Cambridge, MA 02138 USA;

    Harvard Univ, Dept Chem & Chem Biol, 12 Oxford St, Cambridge, MA 02138 USA;

    UCB Biopharma, UCB NewMed, Global Chem, B-1420 Braine Lalleud, Belgium;

    UCB Biopharma, UCB NewMed, Global Chem, B-1420 Braine Lalleud, Belgium;

    Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany;

    Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany|Harvard Univ, Dept Chem & Chem Biol, 12 Oxford St, Cambridge, MA 02138 USA;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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