Mapping the Electronic Structure and the Reactivity Trends for Stabilized α-Boryl Carbanions.

ABSTRACT: The chemistry of stabilized α-boryl carbanions shows remarkable diversity, and can enable many different synthetic routes towards efficient C-C bond formation. The electron-deficient, trivalent boron center stabilizes the carbanion facilitating its generation and tuning its reactivity. Here, the electronic structure and the reactivity trends of a large dataset of α-boryl carbanions are described. DFT-derived parameters were used to capture their electronic and steric properties, computational reactivity towards model substrates, and crystallographic analysis within the Cambridge Structural Dataset. This study maps the reactivity space by systematically varying the nature of the boryl moiety, the substituents of the carbanionic center, the number of α-boryl motifs, and the metal counterion.

SUBMITTER: Maza RJ 

PROVIDER: S-EPMC8457114 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature