Hidden Boron Catalysis: A Cautionary Tale on TMEDA Inhibition
J. G. Macleod, Andrew D. Bage, Leonie M. Meyer, Stephen P. Thomas
Abstract
High Resolution Image Download MS PowerPoint Slide Hidden boron catalysis plagues catalyzed hydroboration reactions, with the “catalyst” acting to mediate the decomposition of HBpin/HBcat to BH 3 which is the actual (hidden) catalyst. N, N, N′, N ′-Tetramethylethylenediamine (TMEDA) has been used to identify hidden boron catalysis through trapping/inhibition. Kinetic analyses showed that TMEDA inhibition is only applicable below 60 °C and that other amine traps are likewise ineffective. Awareness of this temperature limitation reveals widespread hidden catalysis in previous methods and should limit future false negative tests.
Topics & Concepts
ChemistryBoronCatalysisCombinatorial chemistryStereochemistryComputational chemistryMedicinal chemistryOrganic chemistryOrganoboron and organosilicon chemistryOrganometallic Complex Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis