<br/><br/>Ambiphilic compounds have received considerable attention in recent years due to the ability of the Lewis base and Lewis acid to work in unison to activate substrates for increased reactivity. Applications of ambiphilic molecules in catalysis and as bifunctional ligands have proven to be effective in a number of areas. Phosphine boronate esters have been particularly fruitful in this area. C-H borylation of phosphines provides direct access to ambiphilic phosphine boronates. Aryl phosphines can be subjected to iridium-catalyzed C-H borylation upon protection of the phosphine as the borane complex. Upon protection, the phosphine has little effect on the regioselectivity of the C-H borylation, resulting in sterically-controlled functionalization, avoiding positions of the arene ortho to any substituents. The importance of the boron source and additives to the observed reactivity will be outlined, as well as the substrate scope of the reaction.

Sterically-controlled C-H borylation of aryl phosphines

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.