四甲基氟化铵醇加合物用于 SAr 氟化反应。
Tetramethylammonium Fluoride Alcohol Adducts for SAr Fluorination.
机构信息
Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
Department of Radiology, University of Michigan, 1301 Catherine, Ann Arbor, Michigan 48109, United States.
出版信息
Org Lett. 2021 Jun 4;23(11):4493-4498. doi: 10.1021/acs.orglett.1c01490. Epub 2021 May 24.
Nucleophilic aromatic fluorination (SAr) is among the most common methods for the formation of C(sp)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (MeNF·ROH) as fluoride sources for SAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride amyl alcohol (MeNF·AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.
亲核芳香氟化（SAr）是形成 C(sp)-F 键的最常见方法之一。尽管最近取得了许多进展，但这些转化的一个长期存在的限制是需要严格干燥、非质子溶剂条件来保持氟化物的亲核性并抑制副产物的生成。本报告通过利用四甲基氟化铵醇加合物（MeNF·ROH）作为 SAr 氟化的氟源来解决这一挑战。通过系统地调整醇取代基（R），发现四甲基氟化铵戊醇（MeNF·AmylOH）是一种廉价、实用且在温和方便的条件下（在 DMSO 中 80°C，无需干燥试剂或溶剂）适用于 SAr 氟化的试剂。证明了超过 50 种（杂）芳基卤化物和硝基芳烃亲电试剂的底物范围。
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