Derivatization of an Alkylideneborane with BC Bond Cleavage

We present the synthesis, structural characterization, and reactivity of alkylideneborane 2, supported by π-donating N-heterocyclic imino and σ-donating N-heterocyclic carbene (NHC) ligands. The incorporation of these ligands effectively weakens the BC bond strength, leading to enhanced reactivity....

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Published in:Inorganic chemistry 2023-11, Vol.62 (46), p.18820-18824
Main Authors: Han, Jixing, Hu, Chaopeng, Li, Qianli, Liu, Liu Leo, Tung, Chen-Ho, Cui, Ping, Kong, Lingbing
Format: Article
Language:English
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Summary:We present the synthesis, structural characterization, and reactivity of alkylideneborane 2, supported by π-donating N-heterocyclic imino and σ-donating N-heterocyclic carbene (NHC) ligands. The incorporation of these ligands effectively weakens the BC bond strength, leading to enhanced reactivity. Consequently, selective cleavage of the BC bond can be achieved using pyridine-N-oxide, sulfur, and selenium, resulting in the formation of 1,3-dioxa-2,4-diboretane 3, thioxoborane 4, and selenoborane 5, respectively. Furthermore, intriguing BC bond insertions with CO2 and CS2 are observed, affording zwitterionic borenium/fluorenide 6 and dithiaboretane 7. The former species 6 is readily converted to transient oxoborane and imidazolium enolate, showcasing the bora-Wittig reaction of alkylideneborane. This investigation highlights the potential of alkylideneborane as a versatile building block for synthesizing novel organoboron compounds through unconventional transformations.
ISSN:0020-1669
1520-510X
DOI:10.1021/acs.inorgchem.3c03232