论文标题 / Hydrogenation of fluoroarenes: Direct access to all-cis-(multi)fluorinated cycloalkanes
期刊 / Science
发表时间 / 2017-09-01
数字识别码 / 10.1126/science.aao0270
All-cis-multifluorinated cycloalkanes exhibit intriguing electronic properties. In particular, they display extremely high dipole moments perpendicular to the aliphatic ring, making them highly desired motifs in material science. Very few such motifs have been prepared, as their syntheses require multistep sequences from diastereoselectively prefunctionalized precursors. Herein we report a synthetic strategy to access these valuable materials via the rhodium–cyclic (alkyl)(amino)carbene (CAAC)–catalyzed hydrogenation of readily available fluorinated arenes in hexane. This route enables the scalable single-step preparation of an abundance of multisubstituted and multifluorinated cycloalkanes, including all-cis-1,2,3,4,5,6-hexafluorocyclohexane as well as cis-configured fluorinated aliphatic heterocycles.
（导读 阿金）全顺式多氟环烷烃在水平方向上表现出极高的偶极矩，是材料科学中理想的基序材料。本实验开发出通过铑-环烷基氨基卡宾（CAAC）催化氢化己烷中的氟代芳烃，一步反应得到全顺式 1,2,3,4,5,6-多氟环烷烃和顺式构型脂肪族氟代杂环。这种便利的单一步骤合成方法有助于类似合成物的大量生产。