化学
亲核芳香族取代
四甲基铵
亲核细胞
氟化物
酒
加合物
芳基
试剂
取代基
氟
有机化学
溶剂
电泳剂
卤化
药物化学
亲核取代
无机化学
催化作用
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:24
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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