162239-77-2

Upstream product

• 1669-43-8 (E)-4-isopropylbut-3-en-2-one 
• 98-80-6 phenylboronic acid 
• 28557-00-8 phenylzinc chloride 
• 603-33-8 triphenylbismuthane 
• 876953-21-8 (E)-5-methyl-4-phenyl-3-hexen-2-one 
• 853955-69-8 [2-(hydroxymethyl)phenyl]dimethyl(phenyl)silane 
• 5166-53-0 5-methyl-3-hexene-2-one 
• 914400-07-0 (E)-N-methoxy-N,4-dimethyl-3-phenylpent-2-enamide 
• 62751-30-8 (E)-ethyl 4-methyl-3-phenylpent-2-enoate 
• 611-70-1 phenyl isopropyl ketone 
• 17763-67-6 Phenyl triflate 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 1225049-53-5 C₁₃H₁₆O 

Relevant academic research and scientific papers

Preparation of chiral 7,7′-disubstituted BINAPs for Rh-catalyzed 1,4-addition of arylboronic acids

A series of new 7,7′-disubstituted BINAPs were readily prepared starting with an asymmetric catalytic oxidative coupling. They were applied as ligands to rhodium catalyzed 1,4-addition of arylboronic acids to enones, resulting in enantioselectivities of u

Bipyridyl-based diphosphine as an efficient ligand in the rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to α,b-unsaturated ketones

Reactions of α,b-unsaturated ketones with excess arylboronic acids in the presence of a rhodium catalyst generated in situ from Rh(acac)(C2H4)and (S)-P-Phos in dioxane/water at 100 deg C gave high yields of the corresponding products in up to 99 percent ee.

Catalytic asymmetric conjugate reduction with ethanol: A more reactive system Pd(II)-iPr-DUPHOS complex with molecular sieves 4A

We describe herein the catalytic asymmetric conjugate reduction of α,β-unsaturated carbonyl compounds using a novel cationic Pd-iPr-DUPHOS complex. In this reaction, EtOH worked well as a solvent and a reducing agent, and the reaction was compl

Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions

Asymmetric conjugate addition of aryl halides or aryl triflates to electron-deficient olefins was realized by sequential Miyaura borylation and Hayashi-Miyaura conjugate addition in one pot. A nickel-catalyzed borylation of aryl halides or triflates and a rhodium-chiral diene complex catalyzed enantioselective conjugate addition was executed as a pair of relay reactions as a more efficient and greener protocol.

Heterogeneous Chiral Diene-Rh Complexes for Asymmetric Arylation of α,β-Unsaturated Carbonyl Compounds, Nitroalkenes, and Imines

A chiral diene ligand with tertiary alkyl amine-derived secondary amide moiety was immobilized on cross-linked polystyrene (PS) by radical polymerization, which was combined with Rh to form heterogeneous chiral Rh complexes (PS-diene Rh?Cl). PS-diene Rh?Cl catalyzed asymmetric arylation reactions of α,β-unsaturated carbonyl compounds (ketones, esters, and amides), nitroalkenes, and imines afforded the desired products in high yields with excellent enantioselectivities. PS-diene Rh?Cl is stable in air, can be stored for several months, and can be reused more than 10 times without any reduction of either yield or enantioselectivity. We also developed a method of activation of PS-diene Rh?Cl to generate more active species. (Figure presented.).

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

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.

Electronically deficient (Rax,S,S)-F12-C3-TunePhos and its applications in asymmetric 1,4-addition reactions

A novel electronically deficient chiral diphosphine ligand (Rax,S,S)-F12-C3-TunePhos has been concisely synthesized. The electron-poor ligand features both chiral centers and chiral axis bearing fluoro-functional groups on

Cellulose-supported chiral rhodium nanoparticles as sustainable heterogeneous catalysts for asymmetric carbon-carbon bond-forming reactions

Cellulose-supported chiral Rh nanoparticle (NP) catalysts have been developed. The Rh NPs, which were well dispersed on cellulose, catalyzed the asymmetric 1,4-addition of arylboronic acids to enones and enoates, one of the representative asymmetric carbon-carbon bond-forming reactions, in the presence of chiral diene ligands, providing the corresponding adducts in high yields with outstanding enantioselectivities without metal leaching. The solid-state NMR analysis of the chiral NP system directly suggested interactions between the Rh NPs and the chiral ligand on cellulose. This is the first example of using polysaccharide-supported chiral metal nanoparticles for asymmetric carbon-carbon bond-forming reactions.

An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric 1,4-Addition of arylboronic acids to α,β-unsaturated ketones

A new bidentate phosphoramidite (N-Me-BIPAM) based on Shibasaki's N-linked BINOL was synthesized. This ligand appears to be highly effective for rhodium-catalyzed asymmetric conjugated addition of arylboronic acids to α,β-unsaturated enones. The reaction

Expanding the C1-symmetric bicyclo[2.2.1]heptadiene ligand family: Highly enantioselective synthesis of cyclic β-aryl-substituted carbonyl compounds

The efficient preparation of highly enantioenriched cyclic β-aryl-substituted carbonyl compounds has been achieved through the Rh I-catalyzed asymmetric 1,4-addition of an array of arylboronic acids to cyclic α,β-unsaturated carbonyl compounds. In the presence of 0.1 or 0.5 mol-% of the RhI/1g complex, the products of conjugate addition were isolated in 89 to 98%ee and in good to excellent yield.