49833-38-7Relevant academic research and scientific papers
Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant
Wang, Jin,Wei, Chiyu,Li, Xuming,Zhao, Pengyi,Shan, Chuan,Wojtas, Lukasz,Chen, Hao,Shi, Xiaodong
supporting information, p. 5946 - 5950 (2020/04/23)
Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.
Sulfonium Ylides by (3+2) Cycloaddition of Arynes with Vinyl Sulfides: Stereoselective Synthesis of Highly Substituted Alkenes
Li, Yuanming,Mück-Lichtenfeld, Christian,Studer, Armido
supporting information, p. 14435 - 14438 (2016/11/11)
The reaction of in situ generated arynes with vinyl sulfides provides benzannulated sulfonium ylides in a (3+2) cycloaddition. Trapping of the intermediate ylides with electrophiles (proton transfer or a second aryne addition) and subsequent β-elimination give rise to di-, tri-, or tetrasubstituted alkenes with high stereoselectivity. Experimental studies and DFT calculations provide insight into the mechanisms of these cascade reactions.
A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water
Sarrafi, Yaghoub,Sadatshahabi, Marzieh,Alimohammadi, Kamal,Tajbakhsh, Mahmood
supporting information; experimental part, p. 2851 - 2858 (2011/11/06)
The stereoselective formation of C-O, C-S and C-N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic sol
Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes
Ananikov, Valentine P.,Malyshev, Denis A.,Beletskaya, Irina P.,Aleksandrov, Grigory G.,Eremenko, Igor L.
, p. 1993 - 2001 (2007/10/03)
Regioselective Markovnikov-type addition of PhSH to alkynes (HC≡C-R) has been performed using easily available nickel complexes. The non-catalytic side reaction leading to anti-Markovnikov products was suppressed by addition of γ-terpinene to the catalyti
Stereospecific Intermolecular Interception of sp2 Carbanion Intermediates in Nucleophilic Addition to Alkynes
Bury, Adrian,Joag, Sushama D.,Stirling, Charles J. M.
, p. 124 - 125 (2007/10/02)
Addition of sulphur and carbon nucleophiles to methyl propiolate and to phenyl prop-1-ynyl sulphone in the presence of benzaldehyde gives adducts incorporating the three components with a predominantly E-disposition of nucleophile and incorporated benzald
Effect of Catalyst and Solvent on the Stereochemistry of Diels-Alder Reactions Between Cyclopentadiene and 3-Phenylsulfinylprop-2-enoic Acids and Methyl Esters
Proust, Simone M.,Ridley, Damon M.
, p. 1677 - 1688 (2007/10/02)
In Diels-Alder reactions between cyclopentadiene and the isomeric 3-phenylsulfinylprop-2-enoic acids and methyl esters, greatest stereoselectivity (94percent d.e.) results when methyl (Z)-3-phenylsulfinylprop-2-enoate (7) and benzene solvent are used.The
ALUMINIUM-CHLORIDE CATALYZED REACTION OF ALLYLIC SULFIDES WITH METHYL PROPIOLATE: A NOVEL ADDITION REACTION VIA AN IONIC SIGMATROPIC REARRANGEMENT
Hayakawa, Kenji,Kamikawaji, Yoshimasa,Kanematsu, Ken
, p. 2171 - 2174 (2007/10/02)
The aluminium-chloride catalyzed reaction of allylic sulfides with methyl propiolate resulted in the clean formation of novel 1:1 adducts via ionic sigmatropic rearrangements.
