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Facile Synthesis of Thienoacenes via Transition-Metal-Free Ladderization

Mikhail Feofanov, Vladimir Akhmetov, Ryo Takayama, Konstantin Amsharov

2021The Journal of Organic Chemistry16 citationsDOI

Abstract

Herein, we report a facile transition-metal-free approach to sulfur-containing heteroacenes from fluorinated oligophenylenes. Unlike most existing methods, the presented approach is not restricted to simple dibenzothiophene derivatives and thus appears to be a useful tool for the synthesis of extended sulfur-containing heteroacenes. The incorporation of sulfur is unambiguously preprogrammed via the positions of fluorines in the precursors, allowing the selective synthesis of extended thienoacenes with up to 96% yield.

Topics & Concepts

ChemistryDibenzothiopheneSulfurTransition metalYield (engineering)Combinatorial chemistryOrganic chemistryNanotechnologyCatalysisMetallurgyMaterials scienceSulfur-Based Synthesis TechniquesOrganic Chemistry Cycloaddition ReactionsCyclopropane Reaction Mechanisms
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