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

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 witho...

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Detalles Bibliográficos
Autores principales: Hong, Longcheng, Ahles, Sebastian, Heindl, Andreas H, Tiétcha, Gastelle, Petrov, Andrey, Lu, Zhenpin, Logemann, Christian, Wegner, Hermann A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870160/
https://www.ncbi.nlm.nih.gov/pubmed/29623123
http://dx.doi.org/10.3762/bjoc.14.48
Descripción
Sumario: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.

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