Boron trifluoride (BF3) combines with water readily and forms the stable Brønsted superacid complex BF3 monohydrate (BF3-H2O). Many reactions catalyzed by BF3 monohydrate proceed by superelectrophilic activation, the further protonation of non-bonding electron pairs of a monocation that lead to dications which are substantially more reactive than their parent monocation. We are currently exploring the reactivity of BF3 monohydrate and trifluoromethanesulfonic acid (triflic acid), the superacid of choice for studying superacid catalyzed reactions that proceed by superelectrophilic activation. This study compares the reactivity of 2-formylbenzoic acid with arenes catalyzed by either BF3 monohydrate or triflic acid. BF3 monohydrate selectively produces 3-aryl phthalides, compounds possessing a variety of biological activities that include antibacterial activity and the ability to bind to specific human chemokine receptors. In comparison, the stronger triflic acid can further condense 3-aryl phthalides with arenes to produce 10-phenyl anthrones. Analogs to these derivatives have been studied as organic near infrared dyes that have received interest in applications such as high-contrast bioimaging, optical recording, near-Infrared (NIR) photography, and solar cell.

Condensation reactions of 2-formylbenzoic acid with arenes catalyzed by Brønsted superacids

255th National Meeting (2018)

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