Transition metal-free regioselective cross-coupling of azine N-oxides with cymantrenyl lithium

Publication date: 1 September 2018Source: Journal of Organometallic Chemistry, Volume 870Author(s): Alexandra A. Musikhina, Irina A. Utepova, Oleg N. Chupakhin, Valery N. Charushin, Pavel A. SlepukhinAbstractThe facile CC coupling reaction of activated forms of azaaromatics (azine-N-oxides) with cymantrenyl lithium, as a nucleophile, has first been carried out. It has been established that aromatization of intermediate adducts can be realized through either oxidative or eliminative pathways, depending on the structure of the starting azine N-oxide. In particular, the dihydroazinyl intermediates, bearing the additional N(4)-atom relative to the N-oxide group, proved to undergo aromatization through the eliminative pathway. The X-ray studies of 3,6-diphenyl-1,2,4-triazine-5-yl-cymantrene have revealed that it is crystallized in both orthorhombic and monoclinic forms.Graphical abstract

Source: Journal of Organometallic Chemistry - July 5, 2018 Category: Chemistry Source Type: research