Generation of 1,2-azaboretidines via reduction of ADC borane adducts.
نویسندگان
چکیده
Reaction of the acyclic (diamino)carbene (ADC) :C(NiPr2)2 (1) with different dihaloboranes of the type RBX2 (R = Mes, Dur; X = Cl, Br) smoothly afforded a novel class of ADC-stabilized borane adducts. For MesBBr2 however, the reaction did not stop at the adduct level, but an uncommon rearrangement process occurred, which eventually resulted in the formation of a 5-membered boracycle after elimination of mesitylene. Chemical reduction of the ADC borane adducts by KC8 selectively yielded air stable 1,2-azaboretidines. Detailed DFT studies suggest a reduction mechanism involving a highly reactive borylene intermediate, which is converted into the boracycles via a rearrangement/C-H activation sequence.
منابع مشابه
Generation of 1,2-azaboretidines via reduction of ADC borane adducts† †Electronic supplementary information (ESI) available: Experimental, crystallographic, and computational details. CCDC 1042591–1042594. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01077b Click here for additional data file. Click here for additional data file.
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عنوان ژورنال:
- Chemical science
دوره 6 6 شماره
صفحات -
تاریخ انتشار 2015