Sodium mediated deprotonative borylation of arenes using sterically demanding B(CH₂SiMe₃)₃: unlocking polybasic behaviour and competing lateral borane sodiation.

ABSTRACT: The deprotonative metalation of organic molecules has become a convenient route to prepare functionalised aromatic substrates. Amongst the different metallating reagents available, sodium bases have recently emerged as a more sustainable and powerful alternative to their lithium analogues. Here we report the study of the sterically demanding electrophilic trap B(CH₂SiMe₃)₃ for the deprotonative borylation of arenes using NaTMP (TMP = 2,2,6,6-tetramethylpiperidide) in combination with tridentate Lewis donor PMDETA (PMDETA = N,N,N',N'',N''-pentamethyldiethylenetriamine). Using anisole and benzene as model substrates, unexpected polybasic behaviour has been uncovered, which enables the formal borylation of two equivalents of

SUBMITTER: Tortajada A 

PROVIDER: S-EPMC10283504 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature