1,2-Migratory ring expansion of a BN-naphthalene.

ABSTRACT: Organoboranes hold an undeniable value in modern organic chemistry and show ever-growing potential in polymer design and functionalization. Azaborines, in particular, are still being explored as a promising class of organoboron compounds. We investigated the reactivity of a 1,2-azaborine towards Matteson homologation, a cornerstone of organoborane transformations. The azaborine was shown to be reactive towards nucleophiles. Addition of n-BuLi led to exchange of the R group, while addition of chloromethyllithium formed the desired tetracoordinate intermediate. However, rather than homologation, the complex readily underwent ring expansion via migration of the adjacent C(sp²), followed by deborylation. Computational analysis revealed a stable geometry of the azaboron

SUBMITTER: Mediavilla BA 

PROVIDER: S-EPMC12560704 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature