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 (SNH) in non-aro...
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2018-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.14.240 |
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doaj-07374be2081a4584839e6ce2c0eaed752021-02-02T00:30:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-10-011412618262610.3762/bjoc.14.2401860-5397-14-240Transition 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 carboranesLidia A. Smyshliaeva0Mikhail V. Varaksin1Pavel A. Slepukhin2Oleg N. Chupakhin3Valery N. Charushin4Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, RussiaUral Federal University, 19 Mira Str., 620002 Ekaterinburg, RussiaUral Federal University, 19 Mira Str., 620002 Ekaterinburg, RussiaUral Federal University, 19 Mira Str., 620002 Ekaterinburg, RussiaUral Federal University, 19 Mira Str., 620002 Ekaterinburg, RussiaThe 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 (SNH) 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.https://doi.org/10.3762/bjoc.14.240carboranesC–H functionalizationC–H/C–Li cross-coupling2H-imidazole 1-oxidenucleophilic substitution of hydrogen (SNH) |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Lidia A. Smyshliaeva Mikhail V. Varaksin Pavel A. Slepukhin Oleg N. Chupakhin Valery N. Charushin |
| spellingShingle |
Lidia A. Smyshliaeva Mikhail V. Varaksin Pavel A. Slepukhin Oleg N. Chupakhin Valery N. Charushin 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 Beilstein Journal of Organic Chemistry carboranes C–H functionalization C–H/C–Li cross-coupling 2H-imidazole 1-oxide nucleophilic substitution of hydrogen (SNH) |
| author_facet |
Lidia A. Smyshliaeva Mikhail V. Varaksin Pavel A. Slepukhin Oleg N. Chupakhin Valery N. Charushin |
| author_sort |
Lidia A. Smyshliaeva |
| title |
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 |
| title_short |
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 |
| title_full |
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 |
| title_fullStr |
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 |
| title_full_unstemmed |
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 |
| title_sort |
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 |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2018-10-01 |
| description |
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 (SNH) 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. |
| topic |
carboranes C–H functionalization C–H/C–Li cross-coupling 2H-imidazole 1-oxide nucleophilic substitution of hydrogen (SNH) |
| url |
https://doi.org/10.3762/bjoc.14.240 |
| work_keys_str_mv |
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