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

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.

Automated summary

This article describes 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. The reaction retains all the carbon atoms from the three starting materials involved in the assembly.