Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes

The direct C–H functionalization methodology has first been applied to perform transition metal-free C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyllithium. This atom- and step-economical approach, based on one-pot reactions of nucleophilic substitution of hydrogen (SN H) in non-ar...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2018-10, Vol.14 (1), p.2618-2626
Main Authors: Smyshliaeva, Lidia A, Varaksin, Mikhail V, Slepukhin, Pavel A, Chupakhin, Oleg N, Charushin, Valery N
Format: Article
Language:English
Subjects:
2H-imidazole 1-oxide
Boron
carboranes
Chemistry
C–H functionalization
C–H/C–Li cross-coupling
Hydrogen
Imidazole
Letter
Lithium
nucleophilic substitution of hydrogen (SNH)
Oxides
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Summary:The direct C–H functionalization methodology has first been applied to perform transition metal-free C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyllithium. This atom- and step-economical approach, based on one-pot reactions of nucleophilic substitution of hydrogen (SN H) in non-aromatic azaheterocycles, affords novel imidazolyl-modified carboranes of two types (N-oxides and their deoxygenative analogues), which are particularly of interest in the design of advanced materials.
ISSN:2195-951X
1860-5397
1860-5397
DOI:10.3762/bjoc.14.240