Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion

Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion Full article

Journal

Chemical Science
ISSN: 2041-6520 , E-ISSN: 2041-6539

Output data

Year: 2020, Volume: 11, Number: 37, Pages: 10061-10070 Pages count : 10 DOI: 10.1039/d0sc01939a

Authors

Burykina Julia V. ¹ , Shlapakov Nikita S. ^1,2 , Gordeev Evgeniy G. ¹ , König Burkhard ² , Ananikov Valentine P. ¹

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, Russia
2	Institut für Organische Chemie, Universität Regensburg, 93053 Regensburg, Germany

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.

Burykina J.V. , Shlapakov N.S. , Gordeev E.G. , König B. , Ananikov V.P.
Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion
Chemical Science. 2020. V.11. N37. P.10061-10070. DOI: 10.1039/d0sc01939a WOS Scopus OpenAlex

≡ Web of science:	WOS:000573713500029
≡ Scopus:	2-s2.0-85092260188
≡ OpenAlex:	W3044992782