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.
Highlights
The development of efficient and practical methods for synthesis is one of the prime objectives in chemistry
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
We demonstrated a bisboron bidentate Lewis acid (Scheme 1, A) as an efficient catalyst for the IEDDA reaction of 1,2-diazines to access 1,2substituted aromatics [13,14]
Summary
The development of efficient and practical methods for synthesis is one of the prime objectives in chemistry. 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. We demonstrated a bisboron bidentate Lewis acid (Scheme 1, A) as an efficient catalyst for the IEDDA reaction of 1,2-diazines to access 1,2substituted aromatics [13,14].
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