123290-15-3Relevant academic research and scientific papers
First Examples of Episulfone Substitution Reactions via α-Sulfonyl Carbanion Intermediates
Muccioli, Adriano B.,Simpkins, Nigel S.,Mortlock, Andrew
, p. 5141 - 5143 (1994)
Three-membered cyclic sulfones (episulfones) undergo substitution on treatment with base-electrophile mixtures, such as LDA-Me3SiCl and tBu-P4-phosphazene base-PhCHO, to give either substituted episulfones or the corresponding alkenes following loss of SO2.
Alkynes as allylmetal equivalents in redox-triggered C-C couplings to primary alcohols: (Z)-homoallylic alcohols via ruthenium-catalyzed propargyl C-H oxidative addition
Park, Boyoung Y.,Nguyen, Khoa D.,Chaulagain, Mani Raj,Komanduri, Venukrishnan,Krische, Michael J.
, p. 11902 - 11905 (2014/10/15)
The cationic ruthenium catalyst generated upon the acid-base reaction of H2Ru(CO)(PPh3)3 and 2,4,6-(2-Pr) 3PhSO3H promotes the redox-triggered C-C coupling of 2-alkynes and primary alcohols to form (Z)-homoallylic alcohols with good to complete control of olefin geometry. Deuterium labeling studies, which reveal roughly equal isotopic compositions at the allylic and distal vinylic positions, along with other data, corroborate a catalytic mechanism involving ruthenium(0)-mediated allene-aldehyde oxidative coupling to form a transient oxaruthenacycle, an event that ultimately defines (Z)-olefin stereochemistry.
[(NHC)Au1]-catalyzed rearrangement of allylic acetates
Marion, Nicolas,Gealageas, Ronan,Nolan, Steven P.
, p. 2653 - 2656 (2008/02/09)
Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.
An electrochemical coupling of organic halide with aldehydes, catalytic in chromium and nickel salts. the Nozaki-Hiyama-Kishi reaction.
Durandetti,Nedelec,Perichon
, p. 2073 - 2076 (2007/10/03)
[reaction: see text] Electrochemical arylation of arenecarboxaldehydes using an iron sacrificial anode in the presence of chromium and nickel catalysts afforded the corresponding arylated secondary alcohols in moderate to good yields. The chromium and nickel salts as catalysts are obtained by oxidation of a stainless steel rod during a preelectrolysis in 7% and 3%, respectively. The process was also applied to the addition of vinyl halide, allyl acetate, or alpha-chloroester to aromatic aldehydes.
Electroreductive coupling of organic halides with aldehydes catalyzed by nickel(0) complex with 2,2′-bipyridine
Budnikova,Keshner,Kargin
, p. 453 - 456 (2007/10/03)
A method of electrosynthesis of secondary alcohols from aldehydes and organic halides under the action of nickel(0) complexes is proposed. The key stage is addition of σ-complex RNi(I)bipy (bipy is 2,2′-bipyridine) to the aldehyde group.
Rhodium promoted isomerisation of allylic alkoxides: A new method for enolate anion formation
Gazzard, Lewis J.,Motherwell, William B.,Sandham, David A.
, p. 979 - 993 (2007/10/03)
Transition metal mediated isomerisation of allylic alkoxides is presented as a new method for enolate anion generation. The scope and limitations of enolate formation with the catalysts [Rh(dppe)(THF)2]+ClO4- and (Ph3P)3RhCl are explored and the synthetic potential of the methodology demonstrated in the stereoselective formation and reactions of certain ketone and aldehyde enolates.
Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols
Harada, Susumu,Kowase, Noboru,Tabuchi, Nobuhito,Taguchi, Takeo,Dobashi, Yasuo,Dobashi, Akira,Hanzawa, Yuji
, p. 753 - 766 (2007/10/03)
Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1- butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl.
Formation of cyclopropyl carbinols through a highly diastereoselective hydrozirconation of vinyloxirane derivatives
Harada, Susumu,Kowase, Noboru,Taguchi, Takeo,Hanzawa, Yuji
, p. 1957 - 1960 (2007/10/03)
Cyclopropyl carbinol derivatives were efficiently prepared through a highly diastereoseletive hydrozirconation of vinyloxiranes and the intramolecular attack of the generated alkylzirconocene with the inversion of the configuration at the reacting oxirane carbon.
VINYLLITHIUMS FROM BUTYL VINYL TELLURIDES AND BIS-VINYL TELLURIDES
Barros, Simone M.,Comasseto, Joao V.,Berriel, Jorge
, p. 7353 - 7356 (2007/10/02)
Butyl vinyl tellurides and bis-vinyl tellurides furnish vinyllithiums with retention of configuration in good yields upon treatment with n-butyllithium at -78 deg C.
