124244-39-9Relevant academic research and scientific papers
Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis
Theunissen, Cédric,Ashley, Melissa A.,Rovis, Tomislav
, (2019)
Olefin metathesis is now one of the most efficient ways to create new carbon-carbon bonds. While most efforts focused on the development of ever-more efficient catalysts, a particular attention has recently been devoted to developing latent metathesis cat
Preparation of an Immobilized Lipase-Palladium Artificial Metalloenzyme as Catalyst in the Heck Reaction: Role of the Solid Phase
Filice, Marco,Romero, Oscar,Aires, Antonio,Guisan, Jose M.,Rumbero, Angel,Palomo, Jose M.
, p. 2687 - 2696 (2015)
A p-nitrophenylphosphonate palladium pincer was synthesized and selectively inserted by irreversible attachment on the catalytic serine of different commercial lipases with good to excellent yields in most cases. Among all, lipase from Candida antarctica B (CAL-B) was the best modified enzyme. The artificial metalloenzyme CAL-B-palladium (Pd) catalyst was subsequently immobilized on different supports and by different orienting strategies. The catalytic properties of the immobilized hybrid catalysts were then evaluated in two sets of Heck cross-coupling reactions under different conditions. In the first reaction between iodobenzene and ethyl acrylate, the covalent immobilized CAL-B-Pd catalyst resulted to be the best one exhibiting quantitative production of the Heck product at 70°C in dimethylformamide (DMF) with 25% water and particularly in pure DMF, where the soluble Pd pincer was completely inactive. A post-immobilization engineering of catalyst surface by its hydrophobization enhanced the activity. The selectivity properties of the best hybrid catalyst were then assessed in the asymmetric Heck cross-coupling reaction between iodobenzene and 2,3-dihydrofuran retrieving excellent results in terms of stereo- and enantioselectivity.
Applications of 3,3′-disubstituted BINAP derivatives in inter- and intramolecular Heck/Mizoroki reactions
Hopkins, J. Matthew,Gorobets, Evgueni,Wheatley, Bronwen M. M.,Parvez, Masood,Keay, Brian A.
, p. 3120 - 3124 (2006)
A series of 3,3′-disubstituted BINAP ligands are used in asymmetric inter- and intramolecular Heck/Mizoroki reactions and their enantioselectivity compared to BINAP. Georg Thieme Verlag Stuttgart.
First determination of the rate acceleration of a palladium-catalysed coupling reaction by use of high pressure
Hillers, Stephan,Reiser, Oliver
, p. 2197 - 2198 (1996)
The activation volume, ΔV?, reflecting the rate acceleration by pressure, of the coupling reaction between 2,3-dihydrofuran and iodobenzene is determined as -12 ± 2 cm-3 by kinetic measurements at pressures between 1 bar and 8 kbar; moreover, o
The Application of HETPHOX Ligands to the Asymmetric Intermolecular Heck Reaction
Kilroy, Tim G.,Cozzi, Pier Giorgio,End, Nicole,Guiry, Patrick J.
, p. 106 - 110 (2004)
Two new heterocyclic diphenylphosphinooxazolines derived from thiophene and benzothiophene were prepared in moderate to good yield and these, and a range of related HETPHOX ligands, were applied in the intermolecular asymmetric Heck reaction. Phenylation of 2,3-dihydrofuran with the t-butyl-substituted thiophene-oxazoline ligand gave (R)-2-phenyl-2,3-dihydrofuran highly regioselectively with excellent enantioselectivity (91-95% ee) and in good yields (70-97%). In addition, cyclohexenylation of 2,3-dihydrofuran proceeded with enantioselectivities of up to 97% ee in excellent (97%) yields, again with the t-butyl-substituted thiophene-oxazoline ligand proving optimal over a range of reaction conditions investigated.
Synthesis of new chiral benzylically substituted P,N-ligands and their applications in the asymmetric Heck reaction
Hou, Xue-Long,Dong, Da Xuan,Yuan, Ke
, p. 2189 - 2191 (2004)
A series of new chiral P,N-ligands with substituents at the benzylic position has been prepared. Their high catalytic activity is shown in the Pd-catalyzed asymmetric Heck reaction and allylic substitution reaction.
Combined experimental and theoretical study of the mechanism and enantioselectivity of palladium-catalyzed intermolecular heck coupling
Henriksen, Signe T.,Norrby, Per-Ola,Kaukoranta, Paeivi,Andersson, Pher G.
, p. 10414 - 10421 (2008)
The asymmetric Heck reaction using P,N-ligands has been studied by a combination of theoretical and experimental methods. The reaction follows Halpern-style selectivity; that is, the major isomer is produced from the least favored form of the pre-insertio
Palladium nanoparticles in allylic alkylations and heck reactions: The molecular nature of the catalyst studied in a membrane reactor
Dieguez, Montserrat,Pamies, Oscar,Mata, Yvette,Teuma, Emmanuelle,Gomez, Montserrat,Ribaudo, Fabrizio,Van Leeuwen, Piet W. N. M.
, p. 2583 - 2598 (2008)
A series of palladium nanoparticles stabilized by five chiral sugar-based oxazolinyl-phosphite ligands, containing various substituents at the oxazoline and phosphite moieties has been synthesized. They were characterized by transmission electron microsco
BINAP versus BINAP(O) in asymmetric intermolecular Mizoroki-Heck reactions: Substantial effects on selectivities
Woeste, Thorsten H.,Oestreich, Martin
, p. 11914 - 11918 (2011)
2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was employed as chiral ligand in the enantioselective intermolecular Mizoroki-Heck reaction, whereas the use of cognate BINAP(O) (monooxidized BINAP) is unprecedented. The regio- and enantioselectivity of the arylation of representative cyclic alkenes changes dramatically in the presence of hemilabile BINAP(O) instead of BINAP. The arylation of 2,3-dihydrofuran is perfectly regiodivergent (98:2 versus 0:100) and the arylation of cyclopentene is only enantioselective with BINAP(O) [60 versus 10% enantiomeric excess (ee)]. Use of [Pd2(dba)3]·dba (dba=dibenzylideneacetone) instead of Pd(OAc)2 produces as high as 86% ee in the arylation of cyclopentene.
Exploiting the gem-Disubstitution Effect in FcPHOX and HetPHOX P,N Ligands: Synthesis and Applications in Pd-Catalyzed Intermolecular Heck Reactions
McCartney, Dennis,Nottingham, Chris,Müller-Bunz, Helge,Guiry, Patrick J.
, p. 10151 - 10162 (2015)
The synthesis of a range of novel gem-disubstituted and electronically varied thiophene-oxazoline (HetPHOX) ligands and ferrocene-oxazoline (FcPHOX) ligands and their application in the Pd-catalyzed intermolecular asymmetric Heck reaction (IAH) is described. These investigations show that gem-disubstitution of i-Pr-PHOX-type ligands can lead to effective and cost-efficient alternatives to the corresponding t-Bu-PHOX systems. The Pd complexes of these ligands were very effective in the IAH, providing phenylated products in up to 100% conversion with up to 97% ee.
