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Upstream product

• 3262-89-3 triphenylboroxine 
• 260997-38-4 N-(4-chloro-benz-(E)-ylidene)-4-nitro-benzenesulfonamide 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 260997-38-4 C₁₃H₉ClN₂O₄S 
• 63160-16-7 4-nitro-N-(phenylmethylene)benzenesulfonamide 
• 7519-91-7 tris(4-chlorophenyl)boroxine 
• 104-88-1 4-chlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 63160-16-7 4-nitro-N-[(1E)-phenylmethylidene]benzene-1-sulfonamide 
• 934-56-5 trimethyl(phenyl)stannane 

Relevant academic research and scientific papers

Highly Enantioselective Ferrocenyl Palladacycle-Acetate Catalysed Arylation of Aldimines and Ketimines with Arylboroxines

Benzylic N-substituted stereocenters constitute a frequent structural motif in drugs. Their highly enantioselective generation is hence of technical importance. An attractive strategy is the arylation of imines with organoboron reagents. Chiral Rh complexes have reached a high level of productivity for this reaction type. In this article we describe that an electron rich PdIIcatalyst also performs well in the arylation of aldimines, comparable to the best Rh catalysts. The ferrocenyl palladacycle-acetate catalyst allows for a broad substrate scope and very high enantioselectivities. Commonly observed side reactions like aryl–aryl homocouplings and imine hydrolysis could be blocked. Mechanistic studies implicate that a) the acetate ligand is crucial for transmetallation, b) the active catalyst is most likely a palladacycle-OAc monomer, c) the rate limiting step is probably the product release. By added KOAc the arylation could also be applied to ketimines.

A Chiral Disulfoxide Ligand for the Efficient Rhodium-Catalyzed 1,2-Addition of Arylboroxines to N-Tosylarylimines

Enantiomerically pure diarylmethylamines are important building blocks in active pharmaceutical ingredients. Herein, we report a rhodium precatalyst with a chiral disulfoxide ligand that effects the 1,2-addition of arylboroxines to aromatic imines to give high yields and high enantioselectivities of these products. The present paper describes a system that is very simple, where the ease of synthesis of the chiral ligand is combined with low catalyst loadings and reaction conditions that do not need any additives or external base.

Exogenous-Base-Free Palladacycle-Catalyzed Highly Enantioselective Arylation of Imines with Arylboroxines

Enantiomerically pure benzylic amines are important for the development of new drugs. A readily accessible planar-chiral ferrocene-derived palladacycle is shown to be a highly efficient catalyst for the formation of N-substituted benzylic stereocenters; t

C1-symmetric bicyclo[2.2.2]octa-2,5-diene (bod*) ligands in rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to enones and 1,2-addition to N-[(4-nitrophenyl)sulfonyl]imines

A set of ten C1-symmetric chiral bicyclo[2.2.2]octa-2,5-dienes (bod*) 2 (Fig. 1) were tested as ligands in Rh-catalyzed arylation reactions. The 1,4-addition of arylboronic acids to cyclohex-2-en-1-one, cyclopent-2-en-1-one, and tert-butyl cinn

Electronic and steric tuning of chiral diene ligands for rhodium-catalyzed asymmetric arylation of imines

Rhodium-catalyzed asymmetric arylation of imines using electronically and sterically-modified chiral diene ligands gave the corresponding diarylmethylamines in high yield and with high enantioselectivity using just 0.3 mol% of catalyst.

C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines

(Chemical Equation Presented) Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99percent ee) was realized by use of a new C 2-symmetric diene ligand, (1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6- diene (Ph-bnd*), for th

C2-Symmetric bicyclo[3.3.1]nona-2,6-diene and bicyclo[3.3.2]deca-2,6-diene: New chiral diene ligands based on the 1,5-cyclooctadiene framework

As a new type of C2-symmetric chiral diene ligands, which coordinate to a metal by their 1,5-cyclooctadiene framework, we prepared 2,6-disubstituted bicyclo[3.3.1]nona-2,6-diene (bnd*) and bicyclo[3.3.2]deca-2,6-diene (bdd*), and examined their catalytic activity and enantioselectivity for rhodium-catalyzed asymmetric 1,4-addition to α,β-unsaturated ketones and 1,2-addition to N-sulfonylimines. High enantioselectivity of the Ph-bnd* ligand was observed in the addition of phenylboroxine to N-tosylimine and N-4-nitrobenzenesulfonylimine of 4-chlorobenzaldehyde to give phenyl(4-chlorophenyl)methylamines in high enantiomeric excess (98-99% ee).