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Carboxylic acids are abundant in nature, bench stable, cheap, and readily available and thus are ideal feedstocks for organic synthesis. Direct decarboxylation has been widely studied as an effective approach for different synthetic goals such as arylation, alkylation fluorination and vinylation. Decarboxylative elimination for the synthesis of useful olefin products is an under-developed transformation. In this thesis, we outlined the design of a dual catalytic system consisting of an organic photoredox catalyst and a cobaloxime hydrogen evolution catalyst to transform carboxylic acids to olefins via visible-light-promoted decarboxylative elimination under a mild and environmentally friendly condition. The use of the hydrogen evolution catalyst Co(dmgH)2PyCl provides the advantage of avoiding using stoichiometric oxidants for the elimination step. With 2-phenylpropionic acid, a 90% yield of corresponding olefin was obtained. The catalytic system can be applied to other carboxylic acids with excellent yields.
Advisor: Jian Zhang