An air-stable bisboron complex: a practical bidentate Lewis acid catalyst

Abstract

We report an air-stable bisboron complex as an efficient catalyst for the inverse electron-demand Diels–Alder (IEDDA) reaction of 1,2-diazine as well as 1,2,4,5-tetrazine. Its stability towards air and moisture was demonstrated by NMR studies enabling its application in organic transformations without glovebox. A one-pot procedure for its synthesis was developed starting from 1,2-bis(trimethylsilyl)benzene greatly enhancing its practicality. Comparative reactions were carried out to evaluate its catalytic activity in IEDDA reactions of diazine including phthalazine as well as 1,2,4,5-tetrazine.

Keywords

• air-stable catalyst
• bidentate
• bisboron
• diazine
• Diels–Alder
• Lewis acid