Hydrobismuthation: Insertion of Unsaturated Hydrocarbons into the Heaviest Main Group Element Bond to Hydrogen.

ABSTRACT: The bismuth hydride (2,6-Mes₂H₃C₆)₂BiH (1, Mes = 2,4,6-trimethylphenyl), which has a Bi-H ¹H NMR spectroscopic signal at δ = 19.64 ppm, was reacted with phenylacetylene at 60 °C in toluene to yield [(2,6-Mes₂C₆H₃)₂BiC(Ph)=CH₂] (2) after 15 min. Compound 2 was characterized by ¹H, ¹³C NMR, and UV-vis spectroscopy, single crystal X-ray crystallography, and calculations employing density functional theory. Compound 2 is the first example of a hydrobismuthation addition product and displays Markovnikov regioselectivity. Computational methods indicated that it forms via a radical mechanism with an associated Gibbs energy of activation of

SUBMITTER: Mears KL 

PROVIDER: S-EPMC10786065 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature