title: Alkyldisulfanium Salts: Isolable, Electrophilic Sulfur Reagents Competent for Polyene Cyclizations.
abstract: Tools that can effect electrophilic sulfur-promoted cation-π cyclizations are generally lacking, especially using alkylsulfide-based reagents. Herein we report that combining three different 1,2-dithioethers with Cl2and SbCl5generates isolable alkyldisulfanium salts that can effect such reactions. These new reagents can install -SMe, -SEt, and -SCH2CH2CF3in modest, moderate, or good yield on diverse frameworks, including polyenes that terminate with electron-deficient groups. We also show that reagents such as dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) can accomplish similar chemistry.
authors.affiliation: The Scripps Research Institute , Department of Chemistry, 130 Scripps Way, Jupiter, Florida 33458, United States.|The University of Chicago , Department of Chemistry, 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.
authors.forename: Florian T
authors.initials: FT
authors.lastname: Schevenels
authors.affiliation: The University of Chicago , Department of Chemistry, 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.
authors.forename: Minxing
authors.initials: M
authors.lastname: Shen
authors.affiliation: The Scripps Research Institute , Department of Chemistry, 130 Scripps Way, Jupiter, Florida 33458, United States.|The University of Chicago , Department of Chemistry, 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.
authors.forename: Scott A
authors.identifier: 0000-0003-3594-8769
authors.initials: SA
authors.lastname: Snyder
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007202:Indicators and Reagents; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry*; D012492:Salts; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D011090:Polyenes; D012492:Salts; D013457:Sulfur Compounds