HMPA-Free Generation of Trialkylsilyllithium Reagents and Its Applications to the Synthesis of Silylboronic Esters
Martin Oestreich, Hiroto Yoshida, Shintaro Kamio, Taiki Imagawa, Masaaki Nakamoto
Abstract
Abstract Trialkylsilyllithium species have turned out to be facilely generated by treating hexaalkyldisilanes with methyllithium in the presence of tris(N,N-tetramethylene)phosphoric triamide (TPPA) as an activator, which can be trapped by boron electrophiles to afford silylboronic esters including long-awaited Me3Si–B(pin).
Topics & Concepts
ChemistryMethyllithiumElectrophileReagentBoronTrisActivator (genetics)Combinatorial chemistryOrganic chemistryMedicinal chemistryCatalysisBiochemistryGeneOrganoboron and organosilicon chemistryCoordination Chemistry and OrganometallicsAsymmetric Synthesis and Catalysis