124244-39-9Relevant articles and documents
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
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.
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.
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
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.
[Pd/Base/QX] catalyst systems for directing Heck-type reactions
Jeffery, Tuyet,David, Marc
, p. 5751 - 5754 (1998)
Palladium-catalyzed arylation of 2,3-dihydrofuran can be directed at will by an appropriate selection of the [Pd/Base/QX] catalyst systems.
Palladium catalyzed heck arylation of 2,3-Dihydrofuran-effect of the palladium precursor
Morel, Adam,Trzeciak, Anna M.,Pernak, Juliusz
, p. 8402 - 8413 (2014)
Heck arylation of 2,3-dihydrofuran with iodobenzene was carried out in systems consisting of different palladium precursors (Pd2(dba) 3, Pd(acac)2, PdCl2(cod), [PdCl(allyl)] 2, PdCl2(PhCN)
Microwave-Accelerated Ruthenium-Catalyzed Olefin Metathesis
Mayo, Kelly G.,Nearhoof, Eliza H.,Kiddle, James J.
, p. 1567 - 1570 (2002)
(matrix presented) Microwave heating is an efficient method for the acceleration of ring-closing metathesis reactions using ruthenium-based catalysts. The reaction can be rapidly conducted in either ionic liquids, such as 1-butyl-3-methylimidazolium tetrafluoroborate (bmim), or in a microwave transparent solvent (MTS) such as dichloromethane.
Palladium catalyzed coupling reactions of 2,3-dihydrofuran using high pressure conditions
Hillers, Stephan,Reiser, Oliver
, p. 5265 - 5268 (1993)
High presure dramatically influences the palladium catalyzed reaction of 2,3-dihydrofuran (1) and aryl compounds (2-X). An increased activity of the catalyst even in the absence of phosphine ligands has been observed. Nevertheless, using a large excess of
Synthesis, Application and Kinetic Studies of Chiral Phosphite-Oxazoline Palladium Complexes as Active and Selective Catalysts in Intermolecular Heck Reactions
Mazloomi, Zahra,Magre, Marc,Del Valle, Efrem,Pericàs, Miquel A.,Pàmies, Oscar,van Leeuwen, Piet W. N. M.,Diéguez, Montserrat
, p. 1650 - 1664 (2018)
This study identifies new phosphite-oxazoline ligands that have been successfully applied in the palladium-catalyzed intermolecular asymmetric Heck reaction. The design of the new phosphite-oxazoline ligands derives from a previous successful generation of phosphine-oxazoline ligands, by replacing the phosphine group with several π-acceptor biaryl phosphite moieties. With these simple modifications, the new phosphite-based ligands, unlike previous phosphine-oxazoline, not only present a modular design with numerous potential phosphite groups available, but they are also air-stable solids, which can be made in the same number of synthetic steps as the phosphine analogues. The substitution of the phosphine by a biaryl phosphite group extended the range of substrates and triflates sources that can be coupled with regio-, enantioselectivities and activities comparable to the few best ones reported. In addition, the ligands that provided the best selectivities contained an isopropyl oxazoline moiety instead of the tert-butyl group found in the related phosphine-oxazoline ligands, which is made from a much more expensive precursor. In this paper we have also carried out kinetic studies and a Hammett plot analysis to determine the rate determining step of this system in the regime of interest. We suggest a likely explanation for the fast Heck reaction of the phosphite-oxazoline catalysts. (Figure presented.).
The regioselectivity of the asymmetric intermolecular Heck reaction with planar chiral diphosphine-oxazoline ferrocenyl ligands
Tu, Tao,Deng, Wei-Ping,Hou, Xue-Long,Dai, Li-Xin,Dong, Xi-Cheng
, p. 3073 - 3081 (2003)
A series of novel planar chiral diphosphine-oxazoline ferrocenyl ligands were synthesized and used efficiently in the palladium-catalyzed asymmetric intermolecular Heck reaction of 2,3-dihydrofuran with aryl triflate and cyclohexenyl triflate. The tuning of the regioselectivity was realized by means of different palladium precursors and by changing the electronic factor of the ligands. A plausible rationale based on the existed mechanism is provided.
C1-Symmetric Binap Derivative Featuring Single Diferrocenylphosphino-Donor Moiety
Enomoto, Yuuki,Ichiryu, Hiroki,Hu, Hao,Ura, Yasuyuki,Ogasawara, Masamichi
supporting information, p. 1020 - 1024 (2021/05/07)
A C1-symmetric chiral bisphosphine, FcPh-Binap (1), which possesses a single diferrocenylphosphino moiety together with a conventional Ph2P-substituent, was prepared in enantiomerically pure forms. Ligand 1 is sterically less demanding than Fc-Segphos (A)
Chemo-Enzymatic Metathesis/Aromatization Cascades for the Synthesis of Furans: Disclosing the Aromatizing Activity of Laccase/TEMPO in Oxygen-Containing Heterocycles
Risi, Caterina,Zhao, Fei,Castagnolo, Daniele
, p. 7264 - 7269 (2019/10/02)
The unprecedented Trametes versicolor laccase/TEMPO-catalyzed aromatization of 2,5-dihydrofurans to furans is described. A variety of furan derivatives have been synthesized in moderate to high conversions (21-99%) and yields (20-76%) under mild reaction
