78987-46-9Relevant academic research and scientific papers
Silver-catalyzed intermolecular amination of fluoroarenes
Wang, Yu,Wei, Chenlong,Tang, Ruyun,Zhan, Haosheng,Lin, Jing,Liu, Zhenhua,Tao, Weihua,Fang, Zhongxue
supporting information, p. 6191 - 6194 (2018/09/10)
A novel highly selective Ag-catalyzed intermolecular amination of fluoroarenes has been developed. This transformation starts from readily available 4-carbonyl fluorobenzene and NaN3 or other nitrogen-source, via amination followed by C-F bond cleavage, thus affording the desired 4-carbonyl arylamine products under mild conditions. The reaction is accelerated using a small amount of water. This pathway is distinct from a previously reported radical amination reaction.
Ruthenium-catalyzed transfer hydrogenation of amino- and amido-substituted acetophenones
Watson, Andrew J. A.,Fairbanks, Antony J.
supporting information, p. 6784 - 6788 (2013/11/06)
The ruthenium-catalyzed transfer hydrogenation of electron-rich amino-substituted acetophenones is reported. Variation of the reductant, ligands, base, and solvent allowed reaction optimization. A key discovery was the use of 1,4-butanediol as an irreversible reducing agent, which significantly improved the conversion. A range of amino- and amido-substituted aryl ketones were explored, and they all gave the corresponding alcohols in good yield, which demonstrates the wider applicability of this process. The ruthenium-catalyzed reduction of electron-rich amino-substituted acetophenones with 1,4-butanediol as an irreversible reducing agent is reported. Optimization of the conditions and variation of the amino substituent are explored as is the use of amido- and sulfonamidoacetophenones with varying results. Copyright
Ruthenium-catalyzed remote electronic activation of aromatic C-F bonds
Watson, Andrew J. A.,Atkinson, Benjamin N.,Maxwell, Aoife C.,Williams, Jonathan M. J.
supporting information, p. 734 - 740 (2013/04/10)
The tandem isomerization and nucleophilic aromatic substitution of allylic fluoro-substituted benzylic alcohols is described for the first time. In the presence of the ruthenium complex Ru(PPh3)3(CO)(H) 2, 1-(4-fluorophenyl)prop-2-en-1-ol is converted into the corresponding para-amino ketone or para-phenolic substituted ketone. Copyright
Potassium 2,2,5,7,8-pentamethylchroman-6-oxide: A rationally designed base for Pd-catalysed amination
Hoi, Ka Hou,Organ, Michael G.
supporting information; experimental part, p. 804 - 807 (2012/03/11)
This base is just right! A new base, potassium 2,2,5,7,8- pentamethylchroman-6-oxide, for Pd-catalysed amination has been rationally designed that has sufficient basicity to efficiently deprotonate the intermediate aryl palladium ammonium complex, leading to far better rates than obtained with carbonate, which is known to be very mild. At the same time, this new base possesses minimal nucleophilicity to mitigate the degradation of base-sensitive functional groups in the starting materials and products, such as is commonly seen with potassium or sodium tert-butoxide. Copyright
