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tBuOLi-promoted terminal alkyne functionalizations by aliphatic thiols and alcohols

Pramanik, Milan, Mathuri, Ashis and Mal, Prasenjit 2022. tBuOLi-promoted terminal alkyne functionalizations by aliphatic thiols and alcohols. Organic and Biomolecular Chemistry 20 (13) , pp. 2671-2680. 10.1039/D2OB00079B

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Selective radical addition to terminal alkynes is always a difficult task to achieve because it gives a mixture of stereo- and regioisomers. Herein we describe the selective addition of aliphatic thiols or alcohols to N-phenylpropiolamides (terminal alkynes) using lithium tert-butoxide (tBuOLi) in ethanol as a promoter. Mechanistically, it has been shown that the reaction proceeded through the generation of a thiyl radical intermediate, and the amide group in N-phenylpropiolamide could help in the activation of the alkyne, which led to thioacetalization via the formation of a (Z)-selective anti-Markovnikov vinyl sulfide. The (Z)-selectivity during the formation of vinyl sulfides was controlled by an intramolecular sulfur⋯oxygen interaction.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Date of Acceptance: 1 March 2022
Last Modified: 04 Jan 2023 15:30

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