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1,2‐Dialkylation of 1,1‐Arylboryl Alkenes Via Borata‐Alkene Intermediate

Sara González, Oriol Salvadó, Elena Fernández

2022Advanced Synthesis & Catalysis12 citationsDOIOpen Access PDF

Abstract

Abstract We describe here the conjugate addition of tert‐butyllithium to vinyl systems of boronic esters to generate a borata‐alkene intermediate, followed by a sequential S N 2 reaction with alkyl halides, at room temperature. We envisioned this goal through engaged C( sp 3 ) chemical entities avoiding metal catalysts, additives, radical initiators or specific irradiation. This reaction guarantees that the new tetrasubstituted carbon formed retains all the C atoms from the three starting materials involved in the assembly. magnified image

Topics & Concepts

ChemistryAlkeneHalideAlkylConjugateCatalysisCarbon fibersOrganic chemistryComposite materialMathematicsMathematical analysisComposite numberMaterials scienceOrganoboron and organosilicon chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods