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

• considered as nucleophilic substitution of hydrogen (SNH) in non-aromatic N-oxides of 2H-imidazoles 1a–d. It has also been shown that the SNH reactions can be realized via either an "addition–elimination" SNH(AE) mechanism, or through an "addition–oxidation" SNH(AO) scheme to form imidazolyl carbonanes 4a–d

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

• Rakesh Puttreddy,
• Ngong Kodiah Beyeh,
• S. Maryamdokht Taimoory,
• Daniel Meister,
• John F. Trant and
• Kari Rissanen

Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

• , aiding in the binding of polar guests such as N-oxides. Keywords: aromatic N-oxides; C–H···π Interactions; ditopic receptors; endo/exo complexation; host–guest chemistry; resorcinarenes; Introduction Resorcinarenes are macrocyclic compounds with a bowl-shaped cavity stabilised by circular

• shifts’ changes are substantially increased when more electron-donating groups are present on the aromatic N-oxides such as with 5 (two methyl groups) and 9 (two methoxy groups, Figures S5 and S9, Supporting Information File 1). This is expected as the four electron-withdrawing bromine groups on the BrC6

• :1 v/v, no significant chemical shift changes were observed for nine of the twelve pyridine N-oxides. The above results clearly show the strong influence of DMSO in interfering with the host–guest complexation between BrC6 and the aromatic N-oxides. However, with guests such as 5 and 9, endo cavity