258277-16-6

Upstream product

• 14674-38-5 N-(4-methoxybenzylidene)-p-toluenesulfonamide 
• 934-56-5 trimethyl(phenyl)stannane 
• 14674-38-5 (E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide 
• 51608-60-7 phenyl N-tosyl imine 
• 137364-35-3 (4-methoxyphenyl)difluoro(methyl)silane 
• 720-44-5 1-(4-methoxyphenyl)-1-phenylmethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 98-80-6 phenylboronic acid 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 7294-51-1 2,4,6-tris(4-methoxyphenyl)boroxine 
• 7364-21-8 1-methoxy-4-(methoxy(phenyl)methyl)benzene 
• 70-55-3 toluene-4-sulfonamide 
• 3262-89-3 triphenylboroxine 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 138768-32-8 N-((4-methoxyphenyl)(phenyl)methyl)benzamide 
• 1160295-35-1 (4-methoxyphenyl)(phenyl)methyl phenyl sulfone 
• 834-14-0 p-benzylanizole 
• 124494-12-8 1-methoxy-4-(1-phenylbut-3-en-1-yl)benzene 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 1403651-56-8 N-((4-methoxyphenyl)(phenyl)methyl)-N-tosylprop-2-yn-1-amine 
• 53786-86-0 3-((4-methoxyphenyl)(phenyl)methyl)pentane-2,4-dione 

Relevant academic research and scientific papers

Enantioselective palladium-catalyzed arylation of N-tosylarylimines with arylboronic acids using a chiral 2,2′-bipyridine ligand

With the aid of an axially chiral 2,2′-bipyridine ligand, we have successfully developed a palladium-catalyzed method for the enantioselective arylation of N-tosylarylimines, furnishing the chiral diarylmethamines with high yields and enantioselectivities

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.

Development of a CuCl/phosphine system to catalyze phenylation and methylation of N-tosyl aldimines with phenylboronic andmethylboronic acids

The addition of phenylboronic and methylboronic acids to activated aromatic aldimines was demonstrated in the presence of copper(I)-phosphine complexes. The desired products were obtained using copper chloride/phosphine, and potassium fluoride in under toluene reflux, in moderate-to-good yield and a suitable reaction time.

Halogen-Bond-Induced Consecutive Csp3-H Aminations via Hydrogen Atom Transfer Relay Strategy

The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.

A class of chiral nitrogen-containing diene ligands, preparation method and application thereof

The invention belongs to the field of asymmetric synthesis, and relates to a class of chiral nitrogen-containing diene ligands, a preparation method and application thereof, specifically to chiral nitrogen-containing diene ligands with four structures being pairwise enantiomers, wherein the main structural characteristics shared by the ligands are that the ligands have chiral aza[3.3.1] bridge ring skeletons. According to the invention, the chiral nitrogen-containing diene ligands can be used for rhodium-catalyzed asymmetric 1,4-addition reactions on alpha,beta-unsaturated carbonyl compounds by arylboronic acid or asymmetric addition reactions on aromatic imine, wherein the yield and the ee value are medium to good.

Copper-catalyzed synthesis of diarylamines using p-toluene sulfonamides and benzhydrol derivatives under homogeneous borrowing hydrogen conditions

Diarylamines were synthesized using p-toluene sulfonamides with benzhydrol derivatives in the presence of a copper/bisphosphine complex by Borrowing Hydrogen (BH) mechanism, yielding 98% under clean and mild reaction conditions. The use of readily available and cost-effective copper salts, short reaction times, high yield and reaction rates are highlighted.

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.

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.).

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.