191427-03-9

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 17763-67-6 Phenyl triflate 
• 591-50-4 iodobenzene 
• 98-80-6 phenylboronic acid 
• 104516-09-8 1-phenylbuta-2,3-dien-1-ol 
• 108-22-5 Isopropenyl acetate 
• 108-95-2 phenol 

Downstream Products

• 1353720-78-1 C₁₉H₂₆O₄Si 
• 1353720-81-6 C₂₂H₃₂O₆ 

Relevant academic research and scientific papers

C1-Symmetric Binap Derivative Featuring Single Diferrocenylphosphino-Donor Moiety

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)

Efficient Formation of 2,3-Dihydrofurans via Iron-Catalyzed Cycloisomerization of α-Allenols

Herein, we report a highly efficient iron-catalyzed intramolecular nucleophilic cyclization of α-allenols to furnish substituted 2,3-dihydrofurans under mild reaction conditions. A highly diastereoselective variant of the reaction was developed as well, g

Palladium complexes with chiral imidazole ligands as potential catalysts for asymmetric C[sbnd]C coupling reactions

Two palladium complexes of the type [Pd(im)2Cl2] containing chiral imidazole ligands (im?=?1-bornyloxymethylene imidazole, 1-fenchyloxymethylyne imidazole) were synthesized and structurally characterized. The square planar structure of one of the complexes was confirmed by the X-ray analysis. The new palladium complexes were tested as catalysts in various C[sbnd]C bond forming reactions, namely Suzuki–Miyaura, carbonylative Suzuki–Miyaura, asymmetric Heck-type coupling reactions and asymmetric conjugate addition of phenylboronic acid to heterocyclic acceptors. In all the reactions the cross-coupling products were obtained with high yield and selectivity under mild conditions. In case of coupling of 2,3-dihydrofuran with phenylboronic acid ee value ca. 10 was observed.

Enzyme- and Ruthenium-Catalyzed Enantioselective Transformation of α-Allenic Alcohols into 2,3-Dihydrofurans

An efficient one-pot method for the enzyme- and ruthenium-catalyzed enantioselective transformation of α-allenic alcohols into 2,3-dihydrofurans has been developed. The method involves an enzymatic kinetic resolution and a subsequent ruthenium-catalyzed c

Synthesis, characterization and first application of chiral C2-symmetric bis(phosphinite)-Pd(II) complexes as catalysts in asymmetric intermolecular Heck reactions

A series of new chiral C2-symmetric bis(phosphinite) ligands and their palladium(II) complexes have been synthesized and for the first time used as catalysts in the palladium-catalysed asymmetric intermolecular Heck coupling reactions of 2,3-dihydrofuran with iodobenzene or aryl triflate. Under optimized conditions, products were obtained with high conversions and moderate to good enantioselectivities. The new C2-symmetric bis(phosphinite) ligands and their palladium(II) complexes were characterized using multinuclear NMR and Fourier transform infrared spectroscopies and elemental analysis.

Exploiting the gem-Disubstitution Effect in FcPHOX and HetPHOX P,N Ligands: Synthesis and Applications in Pd-Catalyzed Intermolecular Heck Reactions

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.

Photomechanical actuation of ligand geometry in enantioselective catalysis

A catalyst that couples a photoswitch to the biaryl backbone of a chiral bis(phosphine) ligand, thus allowing photochemical manipulation of ligand geometry without perturbing the electronic structure is reported. The changes in catalyst activity and selec

Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

A novel class of chiral phosphanyl-oxazoline (PHOX) ligands with a conformationally rigid cyclopropyl backbone was synthesized and tested in the intermolecular asymmetric Heck reaction. Mechanistic modelling and crystallographic studies were used to predict the optimal ligand structure and helped to design a very efficient and highly selective catalytic system. Employment of the optimized ligands in the asymmetric arylation of cyclic olefins allowed for achieving high enantioselectivities and significantly suppressing product isomerization. Factors affecting the selectivity and the rate of the isomerization were identified. It was shown that the nature of this isomerization is different from that demonstrated previously using chiral diphosphine ligands.

Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran-effect of prolinate salts

Chiral ionic liquids (CILs) containing l-prolinate and l-lactate anions and non-chiral quaternary ammonium cations were employed in the palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran with aryl iodides (iodobenzene, 4-iodotoluene, 2-iodoanisole, 4-iodoanisole, 4-iodoacetophenone). In all the reactions 2-aryl-2,3-dihydrofuran (3) was obtained as the main product with the yield up to 52% at the total conversion reaching 83%. Product 3, 2-phenyl-2,3-dihydrofuran, was obtained with excellent enantioselectivity (>99% ee) in a 6 h reaction with tetrabutylammonium l-prolinate. In the proposed homogeneous reaction Pd(0) nanoparticles are considered as a resting state of the catalyst and a source of soluble palladium species catalyzing the Heck reaction. The yield and stereoselectivity of the Heck reaction are strongly influenced by the kind of non-chiral cations present in CILs. The Royal Society of Chemistry 2013.

BINAP versus BINAP(O) in asymmetric intermolecular Mizoroki-Heck reactions: Substantial effects on selectivities

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.