Immobilized dithianylium salts and ylidene dithianes for the flexible syntheses of selectively labeled building blocks

• Applicants: Professor Dr. Stefan Bräse; Dr. Nicole Jung
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2014 to 2018
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 262361502

With this research project, we want to establish new procedures that allow the specific modification of dithiane derivatives on solid phases. By this, new concepts for the up to now often cumbersome introduction of fluorine and deuterium groups in aliphatic as well as heterocyclic building blocks shall be developed. Depending on the synthetic strategy, a selective construction of CDF2-, CHF2-, CD2F- or CF3-groups will be available on immobilized compounds that may offer further modifications for a diversity oriented synthesis. To expand this concept, the introduction of other electrophiles and nucleophiles in alpha- and beta-position will be investigated in order to synthesize a large number of diverse heterocyclic compounds on solid phases. The herein used dithiane derivatives (dithianylium ions and ylidene dithianes) shall allow the construction of novel functionalities on the core structure via a step by step protocol. In combination with various existing protocols (e.g. cyclizations) for modifications, the concept of immobilized dithiane derivatives provides perfect preconditions for solid phase-supported method development. Most of the method developing experiments will be done in solution and on solid phases to allow the investigation of the success of the reactions in both variants and to enhance basic knowledge in solution and solid phases via the direct comparison. Due to the use of the novel dithiane-based linkers, we will establish the basic knowledge for the selective synthesis of labeled and fluorinated compounds that are required in many fields (of research and beyond) and we will work on novel synthetic procedures for the construction of heterocyclic compounds. The results of the herein described work in form of the analytical data will be added during the project (and at least at its end) to the repository chemotion. Thereby, characterizations of the molecules are visible and available for all interested researchers for free.

• DFG Programme: Research Grants