17438-89-0Relevant academic research and scientific papers
Transfer of alk-1-enyl group from boron to aluminium: A novel way to prepare (E)-alk-1-enyldiisobutylalanes
Hoshi, Masayuki,Shirakawa, Kazuya
, p. 2146 - 2147 (2002)
Treatment of (E)-alk-1-enyldicyclohexylboranes 1 with diisobutylaluminium hydride (DIBAL-H) in the presence of hex-1-ene at room temperature results in transfer of the alk-1-enyl group from boron to aluminium to give (E)-alk-1-enyldiisobutylalanes 2 with retention of configuration at the double bond.
Synthesis and catalytic activity of ruthenium indenylidene complexes bearing unsymmetrical NHC containing a heteroaromatic moiety
Smoleń, Micha?,Ko?nik, Wioletta,Loska, Rafa?,Gajda, Roman,Malińska, Maura,Wo?niak, Krzysztof,Grela, Karol
, p. 77013 - 77019 (2016)
New robust and air stable ruthenium(ii) indenylidene second generation olefin metathesis catalysts with unsymmetrical N-heterocyclic carbene (NHC) ligands were synthesized. Model metathesis reactions were performed in the presence of newly-developed complexes in commercial grade toluene under air, leading to high conversions and good selectivities.
Effect of Silica Gel on the Benzenesulfinic Acid Catalyzed Isomerization of Vinylsilanes. Formation of Silyl Benzenesulfinate
Ochiai, Masahito,Takaoka, Yoshikazu,Ukita, Tatsuzo,Nagao, Yoshimitsu,Fujita, Eiichi
, p. 2346 - 2350 (1989)
A new method for the isomerization of (Z)-vinylsilanes into the E isomers has been developed.In contrast to the facile protodesilylation of vinylsilanes with arenesulfinic acids, use of silica gel as an additive in the reaction of vinylsilanes with benzenesulfinic acid makes possible the selective isomerization of the double-bond geometry by decreasing the rate of the competing protodesilylation.On the basis of the finding that the isomerization proceeds on the surface of the silica gel activated with benzenesulfinic acid and that benzenesulfinic esters such as ethyl, tributylstannyl, and trimethylsilyl benzenesulfinates are also effective as catalysts for the isomerization, the selective isomerization of vinylsilanes was interpreted in terms of the in situ formation of silyl benzenesulfinate bound to a silanol group of the surface of silica gel.
Cyclic alkyl amino carbene (caac) ruthenium complexes as remarkably active catalysts for ethenolysis
Marx, Vanessa M.,Sullivan, Alexandra H.,Melaimi, Mohand,Virgil, Scott C.,Keitz, Benjamin K.,Weinberger, David S.,Bertrand, Guy,Grubbs, Robert H.
, p. 1919 - 1923 (2015)
An expanded family of ruthenium-based metathesis catalysts bearing cyclic alkyl amino carbene (CAAC) ligands was prepared. These catalysts exhibited exceptional activity in the ethenolysis of the seed-oil derivative methyl oleate. In many cases, catalyst turnover numbers (TONs) of more than 100 000 were achieved, at a catalyst loading of only 3 ppm. Remarkably, the most active catalyst system was able to achieve a TON of 340000, at a catalyst loading of only 1 ppm. This is the first time a series of metathesis catalysts has exhibited such high performance in cross-metathesis reactions employing ethylene gas, with activities sufficient to render ethenolysis applicable to the industrial-scale production of linear a-olefins (LAOs) and other terminal-olefin products.
Improved preparation of an olefin metathesis catalyst bearing quaternary ammonium tag (FixCat) and its use in ethenolysis and macrocyclization reactions after immobilization on metal-organic framework (MOF)
Milewski, Mariusz,Kajetanowicz, Anna,Grela, Karol
, p. 73 - 84 (2020)
An optimized synthesis of a key intermediate Ru4 in substantially improved yield of 50% and in scale up to 1 gram was described. Such obtained Ru4 was quantitatively converted into useful quaternary ammonium tagged catalyst Ru1 (FixCat) and immobilized in a metal-organic framework (MOF). Next, two challenging applications, not studied previously with hybrid Ru1@MOF catalyst were attempted. In the case of the RCM reaction yielding a macrocyclic musk lactone, heterogeneous Ru1@MOF exhibited under high-dilution conditions high resistance towards unwanted C-C double bond migration, thus offering superior selectivity as compared to analogous homogeneous catalysts. In ethenolysis of ethyl oleate, Ru1@MOF exhibited only slightly better selectivity as compared to well-known general-purpose Hoveyda-Grubbs SIMes and SIPr catalysts, while it was not able to challenge the benchmark Bertrand-Hoveyda-Grubbs catalyst in this transformation.
From vinyl sulfides, sulfoxides, and sulfones to vinyl transition metal complexes
Farhat, Shahera,Marek, Ilan
, p. 1410 - 1413 (2002)
A transformation with promising versatility: The vinyl zirconium complex 1 can be prepared readily in situ from the educts mentioned in the title and reacts with electrophiles, including other transition metal complexes, to give polysubstituted olefins (s
A Gentler Touch: Synthesis of Modern Ruthenium Olefin Metathesis Catalysts Sustained by Mechanical Force
Mukherjee, Nirmalya,Marczyk, Anna,Szczepaniak, Grzegorz,Sytniczuk, Adrian,Kajetanowicz, Anna,Grela, Karol
, p. 5362 - 5369 (2019)
Mechanochemical synthesis of nine contemporary ruthenium catalysts used for olefin metathesis is described, being the first reported example of formation of Ru carbene organometallic complexes in solid state. Three key organometallic transformations commonly used in the synthesis of the second and third generations of Ru catalysts in solution—phosphine ligand (PCy3) exchange with in situ formed N-heterocyclic carbene (NHC) ligand, PCy3 to pyridine ligand replacement, and benzylidene ligands interchange—were proved to work under mechanochemical conditions, affording the targets in high purity. Mechanochemical approach not only requires less amounts of organic solvent (null for synthesis, only for purification) and is scalable, but also allows for transformations that were reported impossible in the solution phase.
Regio- and Stereoselective Reductive Replacement of Allylic Oxygen, Sulfur, and Selenium Functional Groups by Hydride via Catalytic Activation by Palladium(0) Complexes
Hutchins, Robert O.,Learn, Keith
, p. 4380 - 4382 (1982)
The combination of Pd(Ph3P)4 and LiBHEt3 provides an effective system for reductive removal of allylic ethers, sulfides, sulfones, selenides, and tert-butyldimethylsilyl ethers.
Exploring the reactivity of a ruthenium complex in the metathesis of biorenewable feedstocks to generate value-added chemicals in memory of Professor the Lord Lewis of Newnham: Mentor, encourager, and Ph.D. advisor.
Alexander, Kathryn A.,Paulhus, Emily A.,Lazarus, Gillian M.L.,Leadbeater, Nicholas E.
, p. 74 - 80 (2016)
Tricyclohexylphosphine[4,5-dimethyl-1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene][2-thienylmethylene]ruthenium(II) dichloride proves active for the ring-closing metathesis of linalool and citronellene, the self-metathesis of eugenol, and to some extent the ethenolysis of methyl oleate. Microwave heating and continuous-flow processing have been used as tools for performing the reactions. For the ring-closing metathesis reactions, transition from batch to flow processing for scale-up of the reaction is possible but it proves problematic in the case of cross-metathesis.
Synthesis of selenoxides by oxidation of selenides with superoxide radical anions and 2-nitrobenzenesulfonyl chloride
Tiecco, Marcello,Testaferri, Lorenzo,Temperini, Andrea,Terlizzi, Raffaella,Bagnoli, Luana,Marini, Francesca,Santi, Claudio
, p. 5165 - 5168 (2005)
Alkyl phenyl selenoxides were produced in excellent yields by oxidation of the corresponding selenides with 2-nitrobenzenesulfonyl chloride and potassium superoxide in dry acetonitrile at -15°C.
