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

• Lidia A. Smyshliaeva,
• Mikhail V. Varaksin,
• Pavel A. Slepukhin,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2018, 14, 2618–2626, doi:10.3762/bjoc.14.240

• 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. Keywords: carboranes; C–H functionalization; C–H/C–Li cross-coupling; 2H-imidazole

• mentioned C–H/C–Li coupling reactions successfully as a nucleophilic partner. The direct transition metal-free C–H/C–Li cross-coupling reactions of 2H-imidazole 1-oxides 1a–d with 2 have been found to result in the novel carboranes 4a–d and 5a–d of various architectures. These transformations are able to be

• ), 1.441; C(2A)–C(1A), 1.523; C(2A)–C(12A), 1.532; C(6A)–C(4A), 1.491; C(4A)–N(3A)–C(2A), 108.6; O(1A)–N(1A)–C(2A), 120.4; O(1A)–N(1A)–C(5A), 130.4; C(5A)–C(3A)–C(15), 116.5; C(12A)–C(2A)–N(1A), 107.1; C(1A)–C(2A)–N(3A), 113.0; C(1A)–C(2A)–C(12A), 112.0. C–H/C–Li cross-coupling reactions of 2H-imidazole 1