125640-90-6Relevant articles and documents
Structure-Activity Relationship and Biological Investigation of SR18292 (16), a Suppressor of Glucagon-Induced Glucose Production
Cameron, Michael D.,Griffin, Patrick R.,Kamenecka, Theodore M.,Lin, Hua,Lin, Li,Novick, Scott J.,Puigserver, Pere,Ruiz, Claudia,Sharabi, Kfir,Zhu, Di
supporting information, p. 980 - 990 (2021/02/01)
Despite a myriad of available pharmacotherapies for the treatment of type 2 diabetes (T2D), challenges still exist in achieving glycemic control. Several novel glucose-lowering strategies are currently under clinical investigation, highlighting the need f
Structure-Reactivity Relationship in the Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Imines
Tussing, Sebastian,Kaupmees, Karl,Paradies, Jan
, p. 7422 - 7426 (2016/05/24)
The autoinduced, frustrated Lewis pair (FLP)-catalyzed hydrogenation of 16-benzene-ring substituted N-benzylidene-tert-butylamines with B(2,6-F2C6H3)3 and molecular hydrogen was investigated by kinetic analysis. The pKa values for imines and for the corresponding amines were determined by quantum-mechanical methods and provided a direct proportional relationship. The correlation of the two rate constants k1 (simple catalytic cycle) and k2 (autoinduced catalytic cycle) with pKa difference between imine and amine pairs (ΔpKa) or Hammett's σ parameter served as useful parameters to establish a structure-reactivity relationship for the FLP-catalyzed hydrogenation of imines.
Imine hydrogenation by alkylaluminum catalysts
Hatnean, Jillian A.,Thomson, Jordan W.,Chase, Preston A.,Stephan, Douglas W.
supporting information, p. 301 - 303 (2014/01/06)
Di-isobutylaluminum hydride and tri-iso-butylaluminum (DIBAL 1, TIBAL 2) are shown to be efficient hydrogenation catalysts for a variety of imines at 100 °C and 100 atm of H2, operating via a hydroalumination/ hydrogenolysis mechanism.
Zincocene and dizincocene N-heterocyclic carbene complexes and catalytic hydrogenation of imines and ketones
Jochmann, Phillip,Stephan, Douglas W.
supporting information, p. 8370 - 8378 (2014/07/08)
The N-heterocyclic carbene (NHC) adducts Zn(CpR) 2(NHC)] (CpR=C5HMe4, C 5H4SiMe3; NHC=ItBu, IDipp (Dipp=2,6- diisopropylphenyl), IMes (Mes=mesityl), SIMes) were prepared and shown to be active catalysts for the hydrogenation of imines, whereas decamethylzincocene [ZnCp*2] is highly active for the hydrogenation of ketones in the presence of noncoordinating NHCs. The abnormal carbene complex [Zn(OCHPh2)2(aItBu)]2 was formed from spontaneous rearrangement of the ItBu ligand during incomplete hydrogenation of benzophenone. Two isolated ZnI adducts [Zn2Cp* 2(NHC)] (NHC=ItBu, SIMes) are presented and characterized as weak adducts on the basis of 13C NMR spectroscopic and X-ray diffraction experiments. A mechanistic proposal for the reduction of [ZnCp* 2] with H2 to give [Zn2Cp*2] is discussed.
H2 cleavage, hydride formation, and catalytic hydrogenation of imines with zinc complexes of C5Me5 and N-heterocyclic carbenes
Jochmann, Phillip,Stephan, Douglas W.
supporting information, p. 9831 - 9835 (2013/09/23)
Decamethylzincocene, [ZnCp2], reacts with H2 to give the reduced ZnI compound [Zn2Cp2]. In the presence of coordinating and (more efficiently) of non-coordinating N-heterocyclic carbenes (NHCs), the catalytic hydrogenation of imines with H2 is achieved. The monomeric hydride [Zn(Cp)(H)(SIMes)] is presented and its mechanistic implications are considered. Copyright
