ARYLBORONIC ACIDS WITH INTRAMOLECULAR B-N INTERACTION: CONVENIENT SYNTHESIS THROUGH ortho-LITHIATION OF SUBSTITUTED BENZYLAMINES

Article abstract of DOI:10.1016/S0022-328X(00)99290-8

Ortho-lithiation of N,N-dimethylbenzylamine and reaction with trimethylborate gave the corresponding boronic acid in good yields.The reaction was extended to the synthesis of various aromatic boron compounds with nitrogen-containing substituents in the ortho-position, including a chiral boroxin prepared from (S)-N,N-dimethyl-1-phenylethylamine.From N-Methyl-benzylamine a stable boronium salt was obtained under certain conditions.The spectra of the newly synthesized compounds are discussed.Intramolecular B-N interaction is established by 11B NMR spectroscopy.