Department of Chemistry, University of Michigan , 930 N. University, Ann Arbor, Michigan 48109-1055, United States.
J Am Chem Soc. 2017 Jul 26;139(29):9811-9814. doi: 10.1021/jacs.7b05408. Epub 2017 Jul 13.
We present a strategy to rationally prepare CF transfer reagents at ambient temperature from HCF We demonstrate that a highly reactive CF adduct can be synthesized from alkali metal hydride, HCF, and borazine Lewis acids in quantitative yield at room temperature. These nucleophilic reagents transfer CF to substrates without additional chemical activation, and after CF transfer, the free borazine is quantitatively regenerated. These features enable syntheses of popular nucleophilic, radical, and electrophilic trifluoromethylation reagents with complete recycling of the borazine Lewis acid.
我们提出了一种在环境温度下从 HCF 合理制备 CF 转移试剂的策略。我们证明，在室温下，碱金属氢化物 HCF 和硼烷路易斯酸可以定量生成高反应性的 CF 加合物。这些亲核试剂无需额外的化学活化即可将 CF 转移到底物上，并且在 CF 转移后，游离的硼烷可以定量再生。这些特性使得具有完整硼烷路易斯酸循环的流行亲核、自由基和亲电三氟甲基化试剂的合成成为可能。
