Direct functionalization of C-H bonds by electrophilic anions.

ABSTRACT: Alkanes and [B₁₂X₁₂]^2- (X = Cl, Br) are both stable compounds which are difficult to functionalize. Here we demonstrate the formation of a boron-carbon bond between these substances in a two-step process. Fragmentation of [B₁₂X₁₂]^2- in the gas phase generates highly reactive [B₁₂X₁₁]^- ions which spontaneously react with alkanes. The reaction mechanism was investigated using tandem mass spectrometry and gas-phase vibrational spectroscopy combined with electronic structure calculations. [B₁₂X₁₁]^- reacts by an electrophilic substitution of a proton in an alkane resulting in a B-C bond formation. The product is a dianionic [B₁₂X₁₁C_n

SUBMITTER: Warneke J 

PROVIDER: S-EPMC7519248 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature