Synthesis of Boron Analogues of Enamines via Hydroamination of a Boron-Boron Triple Bond.

ABSTRACT: An N-heterocyclic-carbene-stabilized diboryne undergoes rapid, high-yielding and catalyst-free hydroamination reactions with primary amines, yielding 1-amino-2-hydrodiborenes, which can be considered boron analogues of enamines. The electronics of the organic substituent at nitrogen influence the structure and further reactivity of the diborene product. With electron-rich anilines, a second hydroamination can occur at the diborene to generate 1,1-diamino-2,2-dihydrodiboranes. With isopropylamine, the electronic influence of the alkyl substituent upon the diborene leads to an unprecedented boron-mediated intramolecular N-dearylation reaction of an N-heterocyclic carbene unit.

SUBMITTER: Bruckner T 

PROVIDER: S-EPMC7839459 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature