85211-00-3Relevant academic research and scientific papers
Direct Copper-Catalyzed C-H Monofluoroalkylation of Benzoxazoles with 1-Fluoro-1-haloalkanes
Li, Wei,Varenikov, Andrii,Gandelman, Mark
supporting information, p. 3138 - 3141 (2020/03/13)
The first example of direct C–H bond monofluoroalkylation with 1-fluoro-1-haloalkanes with no adjacent functional groups and with β-hydrogens has been developed. This transformation offers a straightforward route for the synthesis of a series of monofluoroalkylated benzoxazoles.
Tf2O-Promoted Intramolecular Schmidt Reaction of the ω-Azido Carboxylic Acids
Wang, Xue-Juan,Su, Yan,Li, Rui,Gu, Peiming
supporting information, p. 5816 - 5824 (2018/05/14)
A designed Tf2O-promoted intramolecular Schmidt reaction of 2-substituted ω-azido carboxylic acids was demonstrated. Tf2O was used as an activation reagent for the carboxylic acid, and ω-azido anhydride was in situ generated, releasing a molecular TfOH, which acted as an acid promoter for the Schmidt process. A series of 2-substituted pyrrolidines was produced and acetylated for better purification. The strategy was also efficient for conversion of a 4-substituted ω-azido carboxylic acid to the tricyclic lactam.
Ring opening of cyclopropanemonocarboxylates and 1,1- cyclopropanedicarboxylates using samarium(II) diiodide (SmI2)-HMPA-THF system
Yamashita,Okuyama,Ohhara,Kawasaki,Sakai,Nakata,Kawabe,Kusumoto,Ohta
, p. 2075 - 2081 (2007/10/03)
The cyclopropane ring in 2-substituted 1,1-cyclopropanedicarboxylates was regioselectively opened by using samarium(II) diiodide (Sml2) in a hexamethylphosphoric triamide (HMPA)-tetrahydrofuran (THF) (1:10) system under mild and neutral conditions to give (2-substituted ethyl)malonates in moderate to good yields. The cyclopropane ring in 2-substituted cyclopropanecarboxylates or 2-substituted 3- (trimethylsilyl)cyclopropanecarboxylates was similarly cleaved regioselectively by using Sml2 in a HMPA-THF (1:1) system to give 4- arylbutyrates or 4-aryl-3-(trimethylsilyl)butyrates in 16-89% yields. The reaction mechanism of these ring-opening reactions is discussed.
