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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.

SUBMITTER: Hong L

PROVIDER: S-EPMC5870160 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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

Hong Longcheng L Ahles Sebastian S Heindl Andreas H AH Tiétcha Gastelle G Petrov Andrey A Lu Zhenpin Z Logemann Christian C Wegner Hermann A HA

Beilstein journal of organic chemistry 20180313

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 ...[more]

PMID: 29623123

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