Carbon Dioxide Mediated Stereoselective Copper-Catalyzed Reductive Coupling of Alkynes and Thiols

Siti Nurhanna Riduan, Jackie Y. Ying and Yugen Zhang*

*Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos, Singapore 138669, Singapore, Email: ygzhangibn.a-star.edu.sg

S. N. Riduan, J. Y. Ying, Y. Zhang, Org. Lett., 2012, 14, 1761-1767.

DOI: 10.1021/ol3003699

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Abstract

Stereoselectivity in copper-catalyzed hydrothiolation of alkynes is determined by the presence/absence of a CO₂ atmosphere. The reaction system is robust and utilizes inexpensive, readily available substrates. A cyclic alkene/carboxylate copper complex intermediate is proposed as the key step, and an equivalent amount of water is found to play an active role as a proton donor.

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Key Words

Vinyl sulfides

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ID: J54-Y2012-0980