Reported boryl anions (R2B–) often exhibit n–p conjugation between the boron atom and adjacent heteroatoms, with their nucleophilicity being the primary focus. In this work, we present evidence that a...

The synthesis and redox transformations of 6,12-diboraindeno[1,2-b]fluorene (DBIF)─a pentacyclic π-system with diboron incorporation─are reported. In notable contrast to the all-hydrocarbon indenofluo...

In recent years, neutral NHC-stabilized boryl radicals have been investigated as reactive species in various organic transformations. However, cationic boron radicals have been significantly less explored. In addition, boron-centered open-shell species with S > 1/2 have emerged as attractive synthetic targets. In this study, we provide a synthetic route to an NHC-stabilized boryl radical cation as a salt of the weakly coordinating [Al(ORF)4]− (RF = C(CF3)3) anion. The synthetic procedure was extended to dicationic diboron derivatives of Schlenk’s and Thiele’s hydrocarbons with meta- and para-phenylene coupling units between the spin centers. While most known isolable boron biradicals have a singlet ground-state with a thermally accessible triplet state, the boron version of Schlenk’s hydrocarbon occupies a ground-state triplet spin-state, as shown by combined electron paramagnetic resonance spectroscopy and density functional theory studies. Furthermore, initial reactivity studies of the dications with elemental sulfur and diphenyldiselenide are presented.

ConspectusBoron heterocycles represent an important subset of heteroatom-incorporated rings, attracting attention from organic, inorganic, and materials chemists. The empty pz orbital at the boron cen...

Although the activation of elemental sulfur by main group compounds is well-documented in the literature, the products of such reactions are often heterocyclic in nature. However, the isolation and ch...

A Lewis acidic carbodicarbene-stibenium ion mediates C(sp3)−H and C(sp)−H bond breaking of acetonitrile and terminal alkynes in the presence of an organic base. The resulting adducts were reacted wit...

Designing molecules that can undergo late-stage modifications resulting in specific optical properties is useful for developing structure-function trends in materials, which ultimately advance optoele...