1393442-56-2Relevant academic research and scientific papers
Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers
De Bruin, Bas,De Zwart, Felix J.,Li, Zirui,Mathew, Simon,Wolzak, Lukas A.,Zhou, Minghui
supporting information, p. 20501 - 20512 (2021/12/03)
The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.
A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by 1H and 19F NMR Spectroscopy
Groleau, Robin R.,Chapman, Robert S. L.,Ley-Smith, Harry,Liu, Liyuan,James, Tony D.,Bull, Steven D.
, p. 1208 - 1215 (2020/01/02)
A practically simple three-component chiral derivatization protocol has been developed to determine the enantiopurity of eight S-chiral sulfinamides by 1H and 19F NMR spectroscopic analysis, based on their treatment with a 2-formylphenylboronic acid template and enantiopure pinanediol to afford a mixture of diastereomeric sulfiniminoboronate esters whose diastereomeric ratio is an accurate reflection of the enantiopurity of the parent sulfinamide.
AuCl3-Catalyzed Ring-Closing Carbonyl–Olefin Metathesis
Wang, Rui,Chen, Yi,Shu, Mao,Zhao, Wenwen,Tao, Maoling,Du, Chao,Fu, Xiaoya,Li, Ao,Lin, Zhihua
supporting information, p. 1941 - 1946 (2020/02/11)
Compared with the ripeness of olefin metathesis, exploration of the construction of carbon–carbon double bonds through the catalytic carbonyl–olefin metathesis reaction remains stagnant and has received scant attention. Herein, a highly efficient AuCl3-catalyzed intramolecular ring-closing carbonyl–olefin metathesis reaction is described. This method features easily accessible starting materials, simple operation, good functional-group tolerance and short reaction times, and provides the target cyclopentenes, polycycles, benzocarbocycles, and N-heterocycle derivatives in good to excellent yields.
Fluoro-substituted 2-formylphenylboronic acids: Structures, properties and tautomeric equilibria
Kowalska, Kornelia,Adamczyk-Wo?niak, Agnieszka,Gajowiec, Patrycja,Gierczyk, B?azej,Kaczorowska, Ewa,Popenda, ?ukasz,Schroeder, Grzegorz,Sikorski, Artur,Sporzyński, Andrzej
, p. 1 - 8 (2016/05/24)
Four isomeric fluoro-2-formylphenylboronic acids were synthesized and characterized by 1H, 13C, 19F and 17O NMR. Molecular and crystal structure of two compounds was determined by single crystal XRD method. pKa values of all the isomers have been determined by spectrophotometric method and compared with the results for the corresponding benzoxaboroles as well as fluoro- and formylphenylboronic acids. Tautomeric equilibrium with cyclic benzoxaborole form was investigated. The influence of position of fluorine substituents on the properties of investigated compounds is discussed.
BORON-CONTAINING SMALL MOLECULES AS ANTI-INFLAMMATORY AGENTS
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Page/Page column 40, (2008/06/13)
Methods of treating anti-inflammatory conditions through the use of boron-containing small molecules are disclosed.
