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

S−H⋅⋅⋅π Driven Anti‐Markovnikov Thiol‐Yne Click Reaction 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

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

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References (55)

Publisher
Wiley
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201800381
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Asian Journal of Organic ChemistryWiley

Published: Sep 1, 2018

Keywords: ; ; ; ;

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