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Photoinduced three-component coupling reactions of electron deficient alkenes, dienes and active methylene compounds

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Abstract

The irradiation of aqueous acetonitrile solutions, containing electron deficient alkenes, dienes and active methylene compounds along with sodium or cesium carbonate and catalytic amounts of phenanthrene or pyrene, gives rise to the formation of novel three-component coupling products and diene dimers. Cinnamonitrile and benzylidenemalononitrile and its derivatives serve as electron-acceptors; 2,5-dimethyl-2,4-hexadiene and malononitrile anion serve as electron donors in this process. Based on the results of UV-vis absorption spectroscopy and the calculated AG values for single electron transfer (SET), mechanisms are proposed for the coupling reaction involving photoinduced electron transfer (PET) between the electron deficient alkenes and dienes or malononitrile anion via direct excitation of electron deficient alkenes or redox photosensitization using phenanthrene or pyrene serving as a photosensitizer.

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Acknowledgements

This study was financially supported by a Grant-in-Aid for Scientific Research (C) (20550049, 23550047, 26410040, and 17K05777) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan. H. M. is also grateful for financial support from the Mitsubishi Chemical Corporation Fund, the Mazda Foundation, A-STEP (Adaptable and Seamless Technology Transfer Program through target-driven R&D, JST), and the Kanazawa University SAKIGAKE Project. We are also indebted to Professor Tsuyoshi Asakawa and Associate Professor Akio Ohta at the Kanazawa University for permission to use UV absorption and fluorescence spectrophotometers.

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  1. Division of Material Chemistry, Graduate School of Natural Science and Technology Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan

    Hajime Maeda, Hiroshi Takayama & Masahito Segi

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Maeda, H., Takayama, H. & Segi, M. Photoinduced three-component coupling reactions of electron deficient alkenes, dienes and active methylene compounds. Photochem Photobiol Sci 17, 1118–1126 (2018). https://doi.org/10.1039/c8pp00239h

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