Photoinduced proton transfer reactions of diazoalkanes

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Photoinduced proton transfer reactions are an important concept in the development of photoacids and photobases, which find common application in materials chemistry and chemical biology. Applications of photoinduced proton transfer reactions in organic synthesis are even today underdeveloped and mainly limited to the use of high-energy UV light. The understanding and identification of suitable conditions to conduct photoinduced proton transfer reactions under visible light irradiation at ambient conditions is therefore an important task in the development of sustainable synthesis methodology and to understand this conceptual approach towards organic synthesis.In this research project, we plan a systematic study on photoinduced proton transfer reactions of diazoalkanes with different X-H acidic compounds with the aim of understanding the fundamentals and the further exploration of this novel reaction concept. To achieve this goal, we will study the interaction between X-H acidic compounds and diazoalkanes to identify requirements of both reaction partners for efficient proton transfer reactions. These studies comprise detailed mechanistic experiments and basic DFT calculation for the calculation of pKA values. Further applications will involve the exploration of different X-H acidic compounds, such as thiophenols, amides, hydroxamic acids or oximes to expand this concept in a more general way. In a last part, the diazoalkane reaction partner will be studied comprehensively featuring acceptor-only, donor-only or other double substituted diazoalkanes to fully explore this concept from the end of the diazoalkane reaction partner.