Triborane (B₃H₇)-mediated regioselective substitution reactions of pyridine derivatives.

ABSTRACT: There exists an interplay between borane and a Lewis base in their adducts. However, studies on these adducts so far have mainly focused on the different reactions of B-H bonds with limited attention given to the influence of borane on the chemistry of the Lewis base, except for BF₃ and BAr₃. Herein, we have synthesized novel borane adducts with pyridine derivatives, Py·B₃H₇, in which the coordination of B₃H₇ efficiently achieved the intra-molecular charge transfer. The strong B-N bond in these adducts resulted in the formation of stable dearomatic intermediates of pyridine derivatives, confirmed by ¹H and ¹¹B NMR spectroscopy, from which different reactions have transpired to realize C(sp³)-H and C(sp²)-H functionalization under mild conditions. The B₃H₇ pyridine derivatives are stable and do not dissociate or decompose during the reaction process. The high stability of the B-N bond makes this method a good option for boron-containing drugs with potential for use in boron neutron capture therapy (BNCT).

SUBMITTER: Fan ZH 

PROVIDER: S-EPMC11317908 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature