化学
四甲基铵
氟化物
酒
加合物
氟
四甲基氢氧化铵
有机化学
卤素
药物化学
无机化学
烷基
离子
作者
María T. Morales-Colón,Yi Yang See,So Jeong Lee,Peter J. H. Scott,Douglas C. Bland,Melanie S. Sanford
出处
期刊:Organic Letters
[American Chemical Society]
日期:2021-05-24
卷期号:23 (11): 4493-4498
被引量:36
标识
DOI:10.1021/acs.orglett.1c01490
摘要
Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)–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 (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr 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.
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