19466-33-2Relevant academic research and scientific papers
Mizoroki-Heck Cross-Coupling of Bromobenzenes with Styrenes: Another Example of Pd-Catalyzed Cross-Coupling with Potential Safety Hazards
Yang, Qiang,Sane, Neeraj,Klosowski, Daniel,Lee, Melissa,Rosenthal, Tay,Wang, Nick X.,Wiensch, Eric
, p. 2148 - 2156 (2019/11/02)
The potential safety hazards associated with the Mizoroki-Heck cross-coupling of bromobenzenes with styrenes were evaluated. The heat output from the reaction in various solvents was comparable in a variety of solvents; however, the rate of reaction was significantly faster in the presence of water. Thermal stability evaluation of the postreaction mixtures in DMSO and 3:1 DMSO/water by differential scanning calorimetry indicated that the onset temperatures of thermal decomposition were significantly lower than that of neat DMSO. Evaluation of the substrate scope revealed that the substitution pattern on the bromobenzene did not affect the heat output. The reaction rate of electron-deficient bromobenzenes was slower than that of the electron-rich bromobenzenes. In general, substituted styrenes afforded similar magnitudes of exotherms; however, the reaction rate of bromobenzene with 2-methylstyrene was significantly slower than the other studied styrenes. The predicted heat of reaction using the density functional theory method, B3LYP, was in good agreement with the experimental data. Such excellent agreement suggests that this calculation method can be used as a preliminary tool to predict heat of reaction and avoid exothermic reaction conditions. In many of the studied cases, the maximum temperature of a synthesis reaction was considerably higher than the solvent boiling point and thermal decomposition onset temperatures when the reaction was performed in DMSO or 3:1 DMSO/water. It is crucial to understand the thermal stability of the reaction mixture to design the process accordingly and ensure the reaction temperature is maintained below the onset temperature of decomposition to avoid potential runaway reactions.
Rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes
Kang, Lei,Zhang, Feng,Ding, Lin-Ting,Yang, Luo
, p. 100452 - 100456 (2015/12/09)
A rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes to afford 1,2-disubstituted alkenes with good regio- and E-selectivity is developed. This reaction employs readily available aromatic aldehydes as the aryl electrophile counterpart and relies on selected acyl chloride as the crucial additive to activate the rhodium catalyst precursor.
Ligand Control of E/Z Selectivity in Nickel-Catalyzed Transfer Hydrogenative Alkyne Semireduction
Richmond, Edward,Moran, Joseph
, p. 6922 - 6929 (2015/10/05)
A nickel-catalyzed transfer hydrogenative alkyne semireduction protocol that can be applied to both internal and terminal alkynes using formic acid and Zn as the terminal reductants has been developed. In the case of internal alkynes, the (E)- or (Z)-olefin isomer can be accessed selectively under the same reaction conditions by judicious inclusion of a triphos ligand.
Design, synthesis and in vitro biological evaluation of 3-styrylbenzimidamides as potential BACE1 inhibitors
Niu, Yan,Gao, Haifei,Xu, Fengrong,Liang, Lei,Liu, Peng,Wang, Chao,Yang, Guanyu,Sun, Qi,Xu, Ping
, p. 297 - 302 (2013/07/26)
A series of 3-styrylbenzimidamides were synthesized and biologically evaluated in a cell free FRET assay as potential BACE1 inhibitors. Some of the synthesized analogues were discovered to have moderate BACE1 inhibitory activities with IC50 values ranging
