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

• DOI: 10.3762/bjoc.14.48
• Publication Date: 2018-03-13T10:11:02Z
• Authors: Longcheng Hong; Sebastian Ahles; Andreas H Heindl; Gastelle Tiétcha; Andrey Petrov; Zhenpin Lu; Christian Logemann; Hermann A Wegner
• Keywords: Science; air-stable catalyst; Q; diazine; bisboron; Organic chemistry; 01 natural sciences; Lewis acid; Full Research Paper; 3. Good health; 0104 chemical sciences; QD241-441; bidentate; Diels–Alder

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.