2586-35-8Relevant academic research and scientific papers
Silver-Promoted Fluorination Reactions of α-Bromoamides
Mizuta, Satoshi,Kitamura, Kanami,Kitagawa, Ayako,Yamaguchi, Tomoko,Ishikawa, Takeshi
supporting information, p. 5930 - 5935 (2021/02/01)
Silver-promoted C?F bond formation in α-bromoamides by using AgF under mild conditions is reported. This simple method enables access to tertiary, secondary, and primary alkyl fluorides involving biomolecular scaffolds. This transformation is applicable to primary and secondary amides and shows broad functional-group tolerance. Kinetics experiments revealed that the reaction rate increased in the order of 3°>2°>1° α-carbon atom. In addition, it was found that the acidic amide proton plays an important role in accelerating the reaction. Mechanistic studies suggested generation of an aziridinone intermediate that undergoes subsequent nucleophilic addition to form the C?F bond with stereospecificity (i.e., retention of configuration). The synthesis of sterically hindered alcohols and ethers by using AgI is also demonstrated. Examples of reactions of α-bromoamides with O nucleophiles are presented.
Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion
Gray, Erin E.,Nielsen, Matthew K.,Choquette, Kimberly A.,Kalow, Julia A.,Graham, Thomas J. A.,Doyle, Abigail G.
supporting information, p. 10802 - 10805 (2016/09/09)
The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to
Mild decarboxylative activation of malonic acid derivatives by 1,1′-carbonyldiimidazole
Lafrance, Danny,Bowles, Paul,Leeman, Kyle,Rafka, Robert
supporting information; experimental part, p. 2322 - 2325 (2011/06/26)
Chemical equations presented. Malonic acid derivatives undergo unusually mild decarboxylation when treated with N,N′-carbonyldiimidazole (CDI) at room temperature to generate the carbonyl imidazole moiety in high yield, which can be reacted further with a variety of nucleophiles in an efficient one-pot process.
