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S−H⋅⋅⋅π Driven Anti-Markovnikov Thiol-Yne Click Reaction

Choudhuri, Khokan, Pramanik, Milan, Mandal, Arkalekha and Mal, Prasenjit 2018. S−H⋅⋅⋅π Driven Anti-Markovnikov Thiol-Yne Click Reaction. Asian Journal of Organic Chemistry 7 (9) , pp. 1849-1855. 10.1002/ajoc.201800381

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Herein we demonstrate that an anti-Markovnikov selective thiol-yne-click (TYC) reaction could be achieved between phenyl acetylenes and thiophenols by exploiting a newly identified S−H⋅⋅⋅π non-covalent interaction without using any catalysts, additives and solvents. Natural bond orbital (NBO) analyses also supported that S−H⋅⋅⋅π and cooperative π–π stacking interactions helped to promote this regioselective reaction. The hydrothiolated products were isolated in near quantitative yields. Also, the concept of self-sorting was demonstrated when styrene, phenyl acetylene and thiophenols were reacted in one pot. Owing to the stronger S−H⋅⋅⋅π preference of ethynyl≡H over the vinyl=H hydrogen bond, selectively, TYC product formation was found to be dominating over the thiol-ene-click (TEC) product.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 2193-5807
Date of First Compliant Deposit: 10 January 2023
Date of Acceptance: 23 July 2018
Last Modified: 11 Jan 2023 12:46

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