Mono‐ and Di‐Mesoionic Carbene‐Boranes: Synthesis, Structures and Utility as Reducing Agents

Mesoionic 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‐si...

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Bibliographic Details
Published in:European journal of inorganic chemistry Vol. 2021; no. 24; pp. 2417 - 2424
Main Authors: Stein, Felix, Kirsch, Marius, Beerhues, Julia, Albold, Uta, Sarkar, Biprajit
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 25.06.2021
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Subjects:
Alcohols
Aldehydes
Antifungal agents
Boranes
Carbenes
Chemistry
Chemistry, Inorganic & Nuclear
Inorganic chemistry
Mass spectrometry
Mesoionic carbene
NMR spectroscopy
Organometallic compounds
Physical Sciences
Reducing agents
Reduction
Science & Technology
Single crystals
Synthesis
Triazole
Triazoles
Triazolylidene
ELECTRONIC-PROPERTIES
IRIDIUM(III)
Triazole
EXCITED-STATE
CLICK-DERIVED TRIAZOLES
CATALYTIC SYNTHESIS
Triazolylidene
Reduction
ABNORMAL CARBENES
TRIAZOLYLIDENES
Mesoionic carbene
STRUCTURE VALIDATION
LIGANDS
Boranes
METAL-COMPLEXES
ISSN:1434-1948, 1099-0682
Online Access:Get full text
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Summary:Mesoionic 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. A series of MIC‐borane adducts are presented. In one case the unexpected formation of a triazole‐borane adduct through the decomposition of a bitriazolium salt was observed. The compounds were used for the reduction of aldehydes to alcohols in the presence of Lewis acids.
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ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.202100273