TY - PAT
T1 - Organoactinide-, Organolanthanide-, and Organozirconium-Mediated Hydrothiolation of Terminal Alkynes with Aliphatic, Aromatic and Benzylic Thiols
AU - Marks, Tobin
N1 - filingdate: 2010-8-13
issueddate: 2013-12-17
Status: published
attorneydocketnumber: 2009-028-02
PY - 2011/2/17
Y1 - 2011/2/17
N2 - 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) [email protected]
(p) 847.491.4456
AB - 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) [email protected]
(p) 847.491.4456
M3 - Patent
M1 - 8609902
ER -