Game of Isomers: Bifurcation in the Catalytic Formation of Bisbenzothieno[1,4]thiazines with Conformation-Dependent Electronic Properties
datasetposted 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 bisbenzothieno[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 bisbenzothieno[1,4]thiazines.