394-70-7Relevant articles and documents
Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination
Bland, Douglas C.,Lee, So Jeong,Morales-Colón, Mariá T.,Sanford, Melanie S.,Scott, Peter J. H.,See, Yi Yang
supporting information, p. 4493 - 4498 (2021/06/28)
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.
Accelerating palladium-catalyzed C-F bond formation: Use of a microflow packed-bed reactor
Noel, Timothy,Maimone, Thomas J.,Buchwald, Stephen L.
supporting information; experimental part, p. 8900 - 8903 (2011/10/19)
A flow process for Pd-catalyzed C-F bond formation is described. A microreactor with a packed-bed design allows for easy handling of large quantities of insoluble CsF with precise control over reaction times, efficient mixing, and the ability to safely handle elevated temperatures and pressures. A variety of aryl triflates, including heteroaryl ones, were converted into aryl fluorides in short reaction times (see scheme).
The o-Amino-Trifluoromethyl Functionality as a Novel Synthon for 4-Fluoroquinolines
Strekowski, Lucjan,Kiselyov, Alexander S.,Hojjat, Maryam
, p. 5886 - 5890 (2007/10/02)
2-Substituted 4-fluoroquinolines 3 are obtained by the reaction of 2-(trifluoromethyl)aniline (1) with lithium enolates 2 derived from methyl ketones.A similar reaction of 1 with lithium enolate of acetaldehyde produces 4-fluoroquinoline. 1-Fluoro-3-phenyl-4,6-phenanthroline (18) is obtained by treatment of lithium enolate of acetophenone with 4-(trifluoromethyl)quinolin-3-amine (17).By contrast, (Z)-N-carboxamides 10 and 12 are the products of the reaction of 1 with the respective enolate ions derived from 3-pentanone and isobutyl phenyl ketone.A unified mechanism for the formation of quinolines and carboxamides is proposed.