Lewis-base adducts of 9,10-dihydro-9,10-diboraanthracene: ditopic hydroboration reagents and a B–N analogue of triptycene

Abstract

The dimethyl sulfide, pyridazine, or pyrazolide adducts of 9,10-dihydro-9,10-diboraanthracene are potent hydroboration reagents for terminal alkynes; the 1,2-diazene derivatives possess a paddle-wheel structure and are stabilised towards hydrolysis.

How Boron Doping Shapes the Optoelectronic Properties of Canonical and Phenylene‐Containing Oligoacenes: A Combined Experimental and Theoretical Investigation

“…We therefore decided to tackle these issues by quantum chemical calculations. Moreover, we sought to confirm that DBI , a potentially ditopic Lewis acid, forms solely monoadducts with MeCN. Finally, reasons for the large difference in quantum yields of DBP and i DBP , as well as for the lack of emissivity of DBI were uncovered by theoretical means.…”

“…Especially 9,10‐dihydro‐9,10‐diboraanthracenes ( 1 , Figure ), which provide two vicinal boron atoms embedded in a rigid, π‐conjugated cyclic scaffold, are currently receiving attention. As a result of their peculiar structure, compounds 1 act as ditopic Lewis acids that are able to bind ditopic Lewis bases in a chelating manner . Taking advantage of this reactivity, 1 ‐containing compounds have been employed to catalyze inverse electron‐demand Diels–Alder reactions or the dehydrogenation of ammonia‐borane .…”

Poly‐Boron, ‐Silicon, and ‐Gallium Lewis Acids by Hydrometallation of 1,5‐ and 1,8‐Dialkynylanthracenes

“…Jäkle reviewed polymeric organoboron Lewis acids 10. The 9,10‐dihydro‐9,10‐diboraanthracene reported by Wagner et al11 and the anthracenes with boron functions reported by Katz are also interesting,12 as are the applications of such systems (as catalysts) in organic synthesis 13. As mentioned above, most of the poly‐Lewis acids exhibit a flexible organic framework and are potentially capable of complexing a wide range of guest species such as anions or (small) Lewis basic molecules.…”

C‐Halogenated 9,10‐Diboraanthracenes: How the Halogen Load and Distribution Influences Key Optoelectronic Properties

“…Derivatization of the bromoborane at its two boron atoms is facile, for example, with organolithium or Grignard compounds. Alternatively, one can employ Et 3 SiH as a hydride‐transfer reagent to prepare the parent hydroborane (X=Y=H), and subsequently use hydroboration reactions to introduce further organic substituents at the 9,10‐positions . Unfortunately, most of the derivatives obtained these ways are sensitive to air and moisture.…”