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

Lidia A Smyshliaeva; Mikhail V Varaksin; Pavel A Slepukhin; Oleg N Chupakhin; Valery N Charushin

doi:10.3762/bjoc.14.240

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

Beilstein J Org Chem. 2018 Oct 12:14:2618-2626. doi: 10.3762/bjoc.14.240. eCollection 2018.

Authors

Lidia A Smyshliaeva¹, Mikhail V Varaksin^{1

2}, Pavel A Slepukhin^{1

2}, Oleg N Chupakhin^{1

2}, Valery N Charushin^{1

2}

Affiliations

¹ Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russia.
² Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620041 Ekaterinburg, Russia.

Abstract

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 (S_N ^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.

Keywords: 2H-imidazole 1-oxide; C–H functionalization; C–H/C–Li cross-coupling; carboranes; nucleophilic substitution of hydrogen (SNH).