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
CITATION STYLE
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
Mendeley helps you to discover research relevant for your work.