Organoactinide-, Organolanthanide-, and Organozirconium-Mediated Hydrothiolation of Terminal Alkynes with Aliphatic, Aromatic and Benzylic Thiols

Tobin Marks (Inventor)

Research output: Patent

Abstract

Catalyst Method for Production of Vinyl Sulfides for a Variety of Synthetics NU 2009-028 Inventors Tobin J. Marks* Charles J. Weiss Stephen Wobser Abstract Sulfur is a constituent of many important polymeric materials, natural products, and synthetic reagents, providing impetus to devise efficient catalytic methods for sulfur-carbon bond formation. The researchers here utilize novel organoactinide catalysts to selectively add aryl, benzyl, and aliphatic thiols to terminal alkynes - a reaction that can be useful for a variety of synthesis processes. While the chemical process of radical and nucleophilic thiol addition across alkynes in an anti-Markovnikov fashion is well known, synthetic methods using Markovnikov addition for aliphatic thiols have remained a challenge. This methodology offers a clean and quantitative conversion for a broad range of alkyl, aryl, and benzyl thiols and for alkyl, aryl, and vinyl alkynes. These organoactinide catalysts are improved in comparison to the previously-known late transition metal catalysts for the process, as they function with great ease and exhibit a high level of selectivity. Competing, non-catalytic products are detected only occasionally and in negligible quantities under the reaction conditions. The selective catalysts are not as greatly affected by steric hindrances of alkyne substitutents or increasing alkyne encumbrance - a useful property that increases the utility of the molecules. This efficient and selective technology has the potential to benefit a wide variety of chemical production processes. Applications o Production of synthetic materials Advantages o High-functioning, high selectivity for correct products o Catalytic activity minimally affected by steric hindrance Publication Weiss C, Wobser S and Marks T. Lanthanide- and Actinide-Mediated Terminal Alkyne Hydrothiolation for the Catalytic Synthesis of Markovnikov Vinyl Sulfides. Organometallics. 9 Nov 2010. IP Status Issued US Patent No. 8,609,902 Marketing Contact Allan Nader, PhD Invention Manager (e) a-nader@northwestern.edu (p) 847.491.4456
Original languageEnglish
Patent number8609902
StatePublished - Feb 17 2011

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