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Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 51608-60-7 phenyl N-tosyl imine 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 7294-51-1 2,4,6-tris(4-methoxyphenyl)boroxine 
• 14674-38-5 N-(4-methoxybenzylidene)-p-toluenesulfonamide 
• 98-80-6 phenylboronic acid 
• 70-55-3 toluene-4-sulfonamide 
• 3262-89-3 triphenylboroxine 
• 14674-38-5 (E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-52-7 benzaldehyde 
• 1365551-83-2 N-[(S)-(2-bromophenyl)-(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Pd(II)/(S)-t-BuPyOx-catalyzed asymmetric addition of arylboronic acids to N-sulfonyl-arylaldimines

The asymmetric version of Pd(II)/bipyridine-catalyzed nucleophilic addition of arylboronic acids to N-sulfonyl arylaldimines was developed, and excellent asymmetric induction was achieved by the use of chiral pyridinooxazoline ligand (S)-t-BuPyOx. Moistur

Enantioselective Reductive Homocoupling of Allylic Acetates Enabled by Dual Photoredox/Palladium Catalysis: Access to C2-Symmetrical 1,5-Dienes

Transition-metal-catalyzed reductive coupling reactions have emerged as powerful protocols to construct C-C bonds. However, the development of enantioselective C(sp3)-C(sp3) reductive coupling remains challenging. Herein, we report a highly regio-, diastereo-, and enantioselective reductive homocoupling of allylic acetates through cooperative palladium and photoredox catalysis using diisopropylethylamine or Hantzsch ester as a homogeneous organic reductant. This straightforward protocol enables the stereoselective construction of C(sp3)-C(sp3) bonds under mild reaction conditions. A series of C2-symmetrical chiral 1,5-dienes were easily prepared with excellent enantioselectivities (up to >99% ee), diastereoselectivities (up to >95:5 dr), and regioselectivities (up to >95:5 rr). The resultant chiral 1,5-dienes can be directly used as chiral ligands in asymmetric synthesis, and they can be also transformed into other valuable chiral ligands.

Chiral benzene backbone-based sulfoxide-olefin ligands for highly enantioselective Rh-catalyzed addition of arylboronic acids to: N-tosylarylimines

An efficient Rh-catalyzed addition of arylboronic acids to N-tosylarylimines has been developed with chiral benzene backbone-based sulfoxide-olefin ligands, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be more effective.

Synthesizing method of chiral N-Ts diaryl methylamine compound

The invention discloses a synthesizing method of a chiral N-Ts diaryl methylamine compound, and belongs to the technical field of asymmetric synthesis in organic chemistry. The synthesizing method comprises the following steps of using 1eq KF as an alkaline additive, catalyzing by 1.5 mol% of [RhCl(C2H4)2]2 and 3.3 mol% of 2-methoxynapthalene sulfoxide-olefine ligand, using methylbenzene as a solvent, heating to the temperature of 55 DEG C, and performing asymmetric 1,2- addition reaction on arylboronic acid and N-Ts aryl sulfimide, so as to obtain the chiral N-Ts diaryl methylamine. The synthesizing method has the advantages that the obvious influence on the reaction results by the electron effect and steric effect of substituting groups in the reaction primer is avoided, the yield rate of product is 90 to 99%, the enantioselectivity is 95 to 99%ee, showing that the catalysis system has broad protection primer compatibility.

Rhodium-Catalyzed Asymmetric Addition of Organoboronic Acids to Aldimines Using Chiral Spiro Monophosphite-Olefin Ligands: Method Development and Mechanistic Studies

The synthesis of a novel type of chiral spiro monophosphite-olefin (SMPO) ligands based on a hexamethyl-1,1′-spirobiindane scaffold was accomplished starting from Bisphenol C. The optimal ligand could serve as an elegant chiral bidentate ligand in the Rh-catalyzed asymmetric 1,2-addition of organoboronic acids to various acyclic/cyclic aldimines, leading to chiral amines with high yields and excellent enantioselectivities. Detailed stereochemical models for enantioselective induction were elucidated through DFT calculations and postulated the origins of the higher enantioselectivity of phosphite-olefin ligands.

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.

The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions

We have designed the first chiral diene-based metal-organic framework (MOF), E2-MOF, and postsynthetically metalated E2-MOF with Rh(i) complexes to afford highly active and enantioselective single-site solid catalysts for C-C bond fo

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

Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Substituted Amines

The first general palladium-catalyzed, enantioselective three-component synthesis of α-arylamines starting from sulfonamides, aldehydes, and arylboronic acids has been developed. These reactions generate a wide array of α-arylamines with high yields and e