Despite intense studies on bis(NHCs), only flexible or planar scaffolds have been accessed, so far. Herein, we describe synthesis of new tricyclic 7,8-dihydro-1,4-diphosphabarrelenes 1 via addition of non-activated terminal and internal alkenes to an imidazole-based 1,4-diphosphinine diselone. Additionally, the reversibility of these [4+2]-cycloadditions was investigated and will be discussed. 1,4-Diphosphabarrelenes 1 were converted into the corresponding bent bis(imidazolium) salts 2 which can be deprotonated to yield 1,4-diphosphabarrelene-based bis(NHCs) 3 which have been confirmed by NMR spectroscopy. The reactivity of these new bent rigid bis(imidazolium) salts and bis(NHCs) in metal complex formation and towards main group element compounds will be discussed and compared with mono- and bis(NHCs).

From 1,4-diphosphabarrelenes to bent rigid bis(NHCs) – novel opportunities

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ACS Fall 2022

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