Fluorinated compounds are a staple of modern-day chemical innovation, and efficient strategies for their synthesis are highly valuable. In this chemical space, fluoroalkenes continue to be the object of much interest across diverse fields, including drug development and pharmaceuticals with active roles as bioisosteres. Herein, in expanding chemists’ synthetic toolbox for constructing valuable organofluorine compounds, we report a “pipeline” strategy for the synthesis of fluorinated olefins, viz., gem-difluoroalkenyl and monofluoroalkenyl arenes with high E-isomeric selectivity. The advantages of this streamlined synthetic protocol include mild reaction conditions, operational simplicity, broad substrate scope, and good to excellent yields, even at gram scales. Critical to this robust procedure is the use of widely available and inexpensive “scavenger” solid-support Merrifield peptide resin for removing phosphine impurities. Further computational investigations offering clarity into this reactivity are disclosed.

中文翻译：

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通过机理见解简化氟代烯基芳烃合成

氟化化合物是现代化学创新的主要内容，其有效的合成策略非常有价值。在这个化学领域，氟代烯烃仍然是各个领域备受关注的对象，包括药物开发和作为生物电子等排体发挥积极作用的药物。在此，为了扩展化学家构建有价值的有机氟化合物的合成工具箱，我们报告了一种用于合成氟化烯烃（即具有高E异构选择性的偕二氟烯基和单氟烯基芳烃）的“管道”策略。这种简化的合成方案的优点包括反应条件温和、操作简单、底物范围广泛以及良好至优异的产率（即使在克级）。这一稳健程序的关键是使用广泛可用且廉价的“清除剂”固相 Merrifield 肽树脂来去除磷化氢杂质。公开了进一步的计算研究，使这种反应更加清晰。