A focus on anionic boron anthracenes and triptycenes as entry point toward B-doped polyaromatic materials and Lewis acids

This article highlights the recent work of M. Wagner and collaborators on the synthesis, bridgehead functionalization, and photoisomerization of boron-doped triptycene derivative

Stereospecific Allylic Functionalization:The Reactions of Allylboronate Complexes with Electrophiles

Allylboronic esters react readily with carbonyls and imines (π-electrophiles), but are unreactive toward a range of other electrophiles. By addition of an aryllithium, the corresponding allylboronate complexes display enhanced nucleophilicity, enabling addition to a range of electrophiles (tropylium, benzodithiolylium, activated pyridines, Eschenmoser's salt, Togni's reagent, Selectfluor, diisopropyl azodicarboxylate (DIAD), MeSX) in high regio- and stereocontrol. This protocol provides access to key new functionalities, including quaternary stereogenic centers bearing moieties such as fluorine and the trifluoromethyl group. The allylboronate complexes were determined to be 7 to 10 orders of magnitude more reactive than the parent boronic ester.</p