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

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posted on 2019-04-09, 00:00 authored by Arno P. W. Schneeweis, Simone T. Hauer, Daniel A. Lopez, Björn von Dressler, Guido J. Reiss, Thomas J. J. Müller
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 synsyn bis[1]­benzothieno­[1,4]­thiazines.