58627-19-3Relevant academic research and scientific papers
Iridium-Catalyzed Benzylamine C-H Alkenylation Enabled by Pentafluorobenzoyl as the Directing Group
Yang, Xiao,Sun, Rui,Zhang, Chunchun,Zheng, Xueli,Yuan, Maolin,Fu, Haiyan,Li, Ruixiang,Chen, Hua
supporting information, p. 1002 - 1006 (2019/02/19)
The first iridium-catalyzed oxidative alkeynylation of benzylamines with acrylates enabled by a new directing group pentafluorobenzoyl has been developed. The reaction proceeded efficiently in the presence of silver acetate as oxidant and chlorobenzene as
Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control
Khaled, Mohammad B.,El Mokadem, Roukaya K.,Weaver, Jimmie D.
supporting information, p. 13092 - 13101 (2017/09/26)
The photocatalytic C-F functionalization of highly fluorinated arenes is a powerful method for accessing functionalized multifluorinated arenes. The decisive step in the determining regioselectivity in fluorine functionalization is fluoride fragmentation from the radical anion of the multifluorinated arene. To date, the availability of regioisomers has been dictated by the innate electronics of the fluorinated arene, limiting the synthetic utility of the chemistry. This study investigates the remarkable ability of a strategically located hydrogen bond to transcend the normal regioselectivity of the C-F functionalization event. A significant rate acceleration is additionally observed for hydrodefluorination of fluorines that can undergo intramolecular hydrogen bonds that form 5-8-membered cycles with moderately acidic N-H's. The hydrogen bond is expected to facilitate the fragmentation not only by bending the C-F bond of the radical anion out of planarity but also by increasing the exothermicity of the fluoride extrusion step through protonation of the naked fluoride. Finally, the synthetic utility of the method is demonstrated in an expedited synthesis of the trifluorinated α-phenyl acetic acid derivative required for the commercial synthesis of Januvia, an antidiabetic drug. This represents the first synthesis of a commercially important multifluorinated arene via a defluorination strategy and is significantly shorter than the current strategy.
Cooperativity of H-bonding and anion-π interaction in the binding of anions with neutral π-acceptors
Giese, Michael,Albrecht, Markus,Krappitz, Tim,Peters, Marius,Gossen, Verena,Raabe, Gerhard,Valkonen, Arto,Rissanen, Kari
supporting information, p. 9983 - 9985 (2012/11/07)
A rare anion-π complex between bromide and a neutral receptor is reported and related receptor systems are studied with a series of anions. The interaction is observed in the solid state and in solution, and further evidence for it is obtained by a computational study. This journal is The Royal Society of Chemistry 2012.
Oxidation of aldimines to amides by m-CPBA and BF3·OEt2
An, Gwang-Il,Kim, Misoo,Kim, Jin Yeon,Rhee, Hakjune
, p. 2183 - 2186 (2007/10/03)
Several amides were obtained in high yields by an efficient method from the corresponding imines which are readily prepared from aldehydes. This procedure involves the oxidation of aldimines with m-CPBA and BF3·OEt2. In this reaction, the product is strongly influenced by the electron releasing capacity of the aromatic substituent.
