Selectivity control in thiol-yne click reactions: Via visible light induced associative electron upconversion

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Abstract

An associative electron upconversion is proposed as a key step determining the selectivity of thiol-yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products-four types of vinyl sulfides were prepared in high yields and selectivity. We report practically important transition-metal-free regioselective thiol-yne addition and formation of the demanding Markovnikov-type product by a radical photoredox process. The photochemical process was directly monitored by mass-spectrometry in a specially designed ESI-MS device with green laser excitation in the spray chamber. The proposed reaction mechanism is supported by experiments and DFT calculations. This journal is

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Burykina, J. V., Shlapakov, N. S., Gordeev, E. G., König, B., & Ananikov, V. P. (2020). Selectivity control in thiol-yne click reactions: Via visible light induced associative electron upconversion. Chemical Science, 11(37), 10061–10070. https://doi.org/10.1039/d0sc01939a

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