1245819-33-3

Upstream product

• 101671-01-6 1-nitro-2-(4-chlorophenyl)ethylene 
• 98-80-6 phenylboronic acid 
• 102-96-5 (2-nitroethenyl)benzene 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 1679-18-1 4-Chlorophenylboronic acid 

Relevant academic research and scientific papers

Multifunctional isoquinoline-oxazoline ligands of chemical and biological importance

Multifunctional isoquinoline-oxazolines (MIQOXs) were conceived and synthesized from commercially available chiral amino acids. The multifunctional role of MIQOXs was demonstrated by Pd-catalyzed highly enantioselective addition of arylboronic acids to nitrostyrenes, and by the discovery of novel antifungal candidates.

Heterogeneous Rh and Rh/Ag bimetallic nanoparticle catalysts immobilized on chiral polymers

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.

Rhodium-catalyzed Asymmetric Arylation of Nitroalkenes Powered by Simple Chiral Sulfur-Olefin Ligands

An efficient rhodium-catalyzed enantioselective addition of potassium organotrifluoroborates to nitroalkenes powered by simple chiral sulfur-olefin ligands is reported. This protocol is applicable to a broad range of 2-aryl-, alkyl-, and heteroaryl-substituted nitroalkenes, allowing access to diverse chiral β,β-disubstituted nitroethanes in good to excellent yields with high enantioselectivity under mild conditions.

Rhodium-catalyzed asymmetric 1,4-addition reactions of aryl boronic acids with nitroalkenes: Reaction mechanism and development of homogeneous and heterogeneous catalysts

Asymmetric 1,4-addition reactions with nitroalkenes are valuable because the resulting chiral nitro compounds can be converted into various useful species often used as chiral building blocks in drug and natural product synthesis. In the present work, asymmetric 1,4-addition reactions of arylboronic acids with nitroalkenes catalyzed by a rhodium complex with a chiral diene bearing a tertiary butyl amide moiety were developed. Just 0.1 mol% of the chiral rhodium complex could catalyze the reactions and give the desired products in high yields with excellent enantioselectivities. The homogeneous catalyst thus developed could be converted to a reusable heterogeneous metal nanoparticle system using the same chiral ligand as a modifier, which was immobilized using a polystyrene-derived polymer with cross-linking moieties, maintaining the same level of enantioselectivity. To our knowledge, this is the first example of asymmetric 1,4-addition reactions of arylboronic acids with nitroalkenes in a heterogeneous system. Wide substrate generality and high catalytic turnover were achieved in the presence of sufficient water without any additives such as KOH or KHF2 in both homogeneous and heterogeneous systems. Various insights relating to a rate-limiting step in the catalytic cycle, the importance of water, role of the secondary amide moiety in the ligand, and active species in the heterogeneous system were obtained through mechanistic studies.

A nordehydroabietyl amide-containing chiral diene for rhodium-catalysed asymmetric arylation to nitroolefins

A highly enantioselective rhodium catalysed asymmetric arylation (RCAA) of nitroolefins with arylboronic acids is presented using a newly developed, C1-symmetric, non-covalent interacted, phellandrene derived, nordehydroabietyl amide-containing chiral diene under mild conditions. Stereoelectronic effects were studied, suggesting an activation of the bound substrate through the secondary amide as a hydrogen-bond donor.

Palladium-catalyzed asymmetric addition of arylboronic acids to nitrostyrenes

A palladium-catalyzed asymmetric addition of arylboronic acids to nitrostyrene is reported. The catalytic system employing iPr-IsoQuinox as a chiral ligand in MeOH solvent under an air atmosphere provides the chiral diarylsubstituted products in high yields with good enantioselectivities. A variety of functionalized nitrostyrenes can be used, and the method tolerates some variation in arylboronic acid scope. The stereochemical outcome can be explained using a stereochemical model.

Rhodium-catalyzed asymmetric addition of arylboronic acids to β-nitroolefins: Formal synthesis of (S)-SKF 38393

An efficient enantioselective addition of an array of arylboronic acids to various β-nitrostyrenes catalyzed by a novel and reactive rhodium-diene catalyst (S/C up to 1000) was developed, providing β,β- diarylnitroethanes in good to high yields (62-99%) with excellent enantioselectivities (85-97% ee). The method was extended to 2-heteroarylnitroolefins and 2-alkylnitroolefins similarly providing the desired products with high enantioselectivities and yields. The usefulness of this method was demonstrated in the formal synthesis of the enantiomer of the dopamine receptor agonist and antagonist, SKF 38393.

Rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to nitroalkenes using olefin-sulfoxide ligands

An efficient rhodium/olefin-sulfoxide catalyzed asymmetric conjugate addition of organoboronic acids to a variety of nitroalkenes has been developed, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be highly effective and a

Rhodium-catalyzed highly enantioselective addition of arylboronic acids to 2-nitrostyrenes by tert-butanesulfinylphosphine ligand

Particularly picky ligands! An efficient (S/C, substrate/catalyst, up to 500) Rh-catalyzed enantioselective addition of arylboronic acids to 2-nitrostyrenes under mild conditions was developed, which gave excellent yields (up to 99 %) and enantioselectivi

Rhodium-catalyzed asymmetric conjugate addition of organoboronic acids to nitroalkenes using chiral bicyclo [3.3.0] diene ligands

(Figure Presented) Old before l diene: An efficient rhodium/ diene-catalyzed asymmetric conjugate addition of organoboronic acids to challenging nitroalkene substrates that lack α substituents has been developed. Chiral bicyclo[3.3.0] dienes were found to