76217-07-7Relevant articles and documents
Enantioselective Conjugate Addition of Stabilized Arylzinc Iodide to Enones: an Improved Protocol of the Hayashi Reaction
Casotti, Gianluca,Rositano, Vincenzo,Iuliano, Anna
, p. 1126 - 1131 (2020/12/17)
Stabilised arylzinc iodide, prepared by direct insertion of zinc into aryl iodides, were used as nucleophiles in the Hayashi Rh-catalysed enantioselective conjugate addition to enones. The reaction conditions were optimized in the addition of phenylzinc i
Heterogeneous Rh and Rh/Ag bimetallic nanoparticle catalysts immobilized on chiral polymers
Min, Hyemin,Miyamura, Hiroyuki,Yasukawa, Tomohiro,Kobayashi, Shu
, p. 7619 - 7626 (2019/08/20)
The development of heterogeneous chiral catalysts has lagged far behind that of homogeneous chiral catalysts in spite of their advantages, such as environmental friendliness for a sustainable society. We describe herein novel heterogeneous chiral Rh and Rh/Ag bimetallic nanoparticle catalysts consisting of polystyrene-based polymers with chiral diene moieties. The catalysts enable high-to-excellent yields and enantioselectivities to be obtained in asymmetric 1,4-addition reactions of arylboronic acids with α,β-unsaturated carbonyl compounds such as ketones, esters, and amides, and in other asymmetric reactions. The catalysts could be readily recovered by simple filtration and reused; they could also be applied to continuous-flow synthesis. We also discuss the nature of possible reaction species based on XPS analysis.
Ligand-free palladium-catalyzed tandem pathways for the synthesis of 4,4-diarylbutanones and 4,4-diaryl-3-butenones under microwave conditions
Wirwis, Anna,Trzeciak, Anna M.
, (2019/03/20)
Two efficient Pd-catalyzed tandem pathways for the synthesis of 4,4-diaryl-2-butanones and 4,4-diaryl-3-buten-2-ones were elaborated. The first step in both procedures was the Heck coupling of methyl vinyl ketone (MVK) and various aryl iodides leading to 4-aryl-3-buten-2-one with the yield of up to 92% in 1?hr. The second step performed with the same catalyst and a new portion of aryl iodide in the presence K2CO3 as a base produced 4,4-diaryl-3-buten-2-ones in high yield. Reaction selectivity changed completely to saturated 4,4-diaryl-2-butanones, reductive Heck products, when a tertiary amine was used instead of K2CO3. Due to the application of microwave irradiation (MW), the desired products were obtained in high yield in a short time (4?hr), using 0.5?mol% of the Pd (OAc)2 catalyst without additional ligands.
Hydrotalcite-supported palladium nanoparticles as catalysts for the hydroarylation of carbon-carbon multiple bonds
Di Nicola,Arcadi,Gallucci,Mucciante,Rossi
supporting information, p. 1952 - 1957 (2018/02/09)
Palladium nanoparticles supported on Mg/Ca hydrotalcites catalyze the hydroarylation reaction of different alkynes and alkenes with aryl iodides under air in MeCN. The reaction of tertiary propargylic alcohols (1) with aryl iodides (2) yields, stereoselectively, γ,γ-diarylallylic alcohols (3) in moderate to high yields and high selectivity. Also, the HT/Pd hydroarylation reaction with aryl iodides was attempted on norbornene and α,β-unsaturated ketones affording, respectively, exo-aryl bicyclo[2.2.1]heptanes and β-aryl ketones in moderate to high yields. All the reactions described benefit from using a heterogeneous catalyst with evident advantages in terms of reaction purification and recyclability of the catalyst.
Importance of the Reducing Agent in Direct Reductive Heck Reactions
Raoufmoghaddam, Saeed,Mannathan, Subramaniyan,Minnaard, Adriaan J.,de Vries, Johannes G.,de Bruin, Bas,Reek, Joost N. H.
, p. 266 - 272 (2017/12/07)
The role of the reductant in the palladium N-heterocyclic carbene (NHC) catalyzed reductive Heck reaction and its effect on the mechanism of the reaction is reported. For the first time in this type of transformation, the palladium-NHC-catalyzed reductive
Electronic and Steric Tuning of an Atropisomeric Disulfoxide Ligand Motif and Its Use in the Rh(I)-Catalyzed Addition Reactions of Boronic Acids to a Wide Range of Acceptors
Zhao, Guang-Zhen,Foster, Daven,Sipos, Gellért,Gao, Pengchao,Skelton, Brian W.,Sobolev, Alexandre N.,Dorta, Reto
, p. 9741 - 9755 (2018/09/06)
A novel chiral disulfoxide ligand pair bearing fluorine atoms at the 6 and 6′ position of its atropisomeric backbone, (M,S,S)- and (P,S,S)-p-Tol-6F-BIPHESO, was synthesized. Complexation to a rhodium(I) precursor gave rise to μ-Cl- and μ-OH-bridged rhodiu
A diastereomeric pair of sulfoxide-containing chiral MOP-type ligands: Preparation and application to rhodium-catalyzed asymmetric 1,4-addition reactions
Hoshi, Takashi,Fujita, Masataka,Matsushima, Shouta,Hagiwara, Hisahiro,Suzuki, Toshio
supporting information, p. 800 - 802 (2018/06/12)
(R,SS)-Sulfoxide-MOP (L2) and (R,RS)-sulfoxide-MOP (L3) were developed as a diastereomeric pair of sulfoxide-containing chiral MOP-type ligands. These two ligands also represent the first monosulfoxide analogues of BINAP. The chiral ligand L2 was successfully applied to the highly enantioselective rhodium-catalyzed 1,4-addition between α,β-unsaturated ketones or esters and arylboronic acids, and exhibited a broad substrate scope when the reaction was performed using 1.5 mol% Rh in cyclohexane/H2O (10:1) at 40 °C under mild basic conditions.
Aqueous Asymmetric 1,4-Addition of Arylboronic Acids to Enones Catalyzed by an Amphiphilic Resin-Supported Chiral Diene Rhodium Complex under Batch and Continuous-Flow Conditions
Shen, Guanshuo,Osako, Takao,Nagaosa, Makoto,Uozumi, Yasuhiro
, p. 7380 - 7387 (2018/07/29)
A rhodium-chiral diene complex immobilized on amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin (PS-PEG-diene?-Rh) has been developed. The immobilized rhodium-chiral diene complex (PS-PEG-diene?-Rh) efficiently catalyzed the asymmetric 1,4-addition of various arylboronic acids to cyclic or linear enones in water under batch conditions to give the corresponding β-arylated carbonyl compounds in excellent yields and with excellent enantioselectivity. The catalyst was readily recovered by simple filtration and reused 10 times without loss of its catalytic activity and enantioselectivity. Moreover, a continuous-flow asymmetric 1,4-addition in a flow reactor containing PS-PEG-diene?-Rh proceeded efficiently at 50 °C with retention of high enantioselectivity. Long-term continuous-flow asymmetric 1,4-addition during 12 h readily gave the desired product on a 10 g scale with high enantioselectivity.
Stable and Reusable Palladium Nanoparticles-Catalyzed Conjugate Addition of Aryl Iodides to Enones: Route to Reductive Heck Products
Parveen, Naziya,Saha, Rajib,Sekar, Govindasamy
, p. 3741 - 3751 (2017/11/15)
An efficient, binaphthyl-backbone-stabilized palladium nanoparticles (Pd-BNP) catalyst for the 1,4-addition of aryl halides to enones has been developed. The scope of the reaction has been studied with various substituted and sterically hindered aryl hali
Deodoration sulfonamide monophosphine ligand, its full configuration preparation method and application (by machine translation)
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Paragraph 0142-0145, (2017/08/14)
The present invention provides a central chiral Asia sulfonamide monophosphine ligand and its preparation method, 2 - disubstituted base phosphine base aryl (heteroaryl) formaldehyde (ketone) 2 and deodoration sulfonamide 3 condensation to obtain compound 4, with nucleophiles to obtain compound 1; or aldehyde (ketone) 5 and deodoration sulfonamide 3 condensation to obtain the imine 6, with 2 - disubstituted base phosphine base aryl (heteroaryl) metal reagent reaction to obtain compound 1; or imine 6 with 2 - disubstituted phosphonate acyl aryl (heteroaryl) metal reagent to obtain the compound to reduction to obtain compound 1; or 2 - substituted phosphonate acyl aryl (heteroaryl) formaldehyde (ketone) 8 and deodoration sulfonamide 3 condensation to obtain the imine compound 9, with nucleophiles to obtain compound 7 re-reduction to obtain compound 1. By using different chiral Asia sulfonamide and different metal reagent, conveniently obtain the (R, R), (R, S), (S, S) or (S, R) configuration of four optical pure compound. This type of framework is simple, synthesis is convenient, easy to change, and can be applied to various metal catalytic asymmetric reaction, has very high reaction activity and stereo selectivity. (by machine translation)
