Abstract
AbstractMesoionic carbenes (MIC) of the 1,2,3‐triazol‐5‐ylidene type are currently popular ligands in organometallic chemistry. Their use in main group chemistry has been rather limited. In this contribution we present mono‐ and di‐MIC‐boranes with MICs based on triazolylidenes. The synthesis involves in‐situ deprotonation of the corresponding triazolium salts and their reaction with boranes to form the desired compounds. Whereas this reaction route worked well for all triazolium salts derived from the 1,4‐regioisomer of the triazoles, for the methlyene‐bridged bi‐triazolium salt derived from a 1,5‐substiuted triazole, we observed the unexpected decomposition of the bi‐triazolium and the formation of a triazole‐borane with a new N−B bond. All compounds were characterized via multinuclear NMR spectroscopy, mass spectrometry, and single crystal X‐ray diffraction. Furthermore, the MIC‐boranes were used as reducing agents for the reduction of the C=O of aldehydes to the corresponding alcohols.
Highlights
Mesoionic carbenes (MIC) of the 1,2,3-triazol-5-ylidene type are currently popular ligands in organometallic chemistry
For mono-triazolium salts and the bi-triazolium salts derived from the 1,4-substituted triazoles, the reactions led to the desired formation of the mono- and the bi-MIC-borane adducts
This is the first example of a bi-MIC-bi-borane adduct based on MICs of the 1,2,3-triazol-5-ylidene type
Summary
We report on the reaction of a methylene-bridged bi1,2,3-triazol-4-ylidene, derived from a 1,5-disubstituted-1,2,3triazole, with BH3. The difference in the reactivities of these different isomers of triazolylidenes will be discussed. Results from multi-nuclear NMR spectroscopy, mass spectrometry, and single crystal X-ray diffraction are reported. We show the utility of the MIC-borane adducts in the reduction of the C=O group of aldehydes to the corresponding alcohols
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