Game of Isomers: Bifurcation in the Catalytic Formation of Bis[1]benzothieno[1,4]thiazines with Conformation-Dependent Electronic Properties

摘要

Two regioisomers of bis[1]benzothieno[1,4]thiazine are unexpectedly obtained by tuning the catalytic conditions of the intermolecular-intramolecular Buchwald-Hartwig amination. Mechanistic insights and evidence of intermediates support a conclusive mechanistic rationale. Furthermore, a computationally based study on the influence of conformational aspects on the HOMO energy level of anellated 1,4-thiazine paves the way to enhance the electronic properties, thus successfully achieving higher luminescent and easier oxidizable syn-syn bis[1]benzothieno[1,4]thiazines.