40462-76-8

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 91-00-9 Benzhydrylamine 
• 74-11-3 para-chlorobenzoic acid 
• 88229-32-7 N-benzhydryl-4-chlorobenzamide 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

• 112254-35-0 Benzoic acid (E)-2-(benzhydrylidene-amino)-2-(4-chloro-phenyl)-1-phenyl-vinyl ester 
• 359414-53-2 [(benzhydryl-amino)-(4-chloro-phenyl)-methyl]-phosphonic acid diethyl ester 
• 1283154-28-8 N-benzhydryl-1-(4-chlorophenyl)-1-[dimethyl(phenyl)silyl]methanamine 
• 16656-60-3 [amino-(4-chlorophenyl)methyl]phosphonic acid 
• 1100245-90-6 benzhydryl-[1-(4-chlorophenyl)-2,2,2-trifluoroethyl]amine 
• 126529-67-7 [Amino-(4-chloro-phenyl)-methyl]-phosphinic acid 

Relevant academic research and scientific papers

Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis

The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α-aminonitriles and α-aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α-functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the thiourea catalyst can be recycled and reused.

2-Azaallyl Anion Initiated Ring-Opening Polymerization of N-Sulfonyl Aziridines: One-Pot Synthesis of Primary Amine-Ended Telechelic Polyaziridines

Using the easily accessible 2-azaallyl anions as initiators, the one-pot synthesis of well-defined primary amine-ended telechelic polyaziridines (α-NH2 PAzs) has been achieved through the ring-opening polymerization (ROP) of N-sulfonyl aziridines followed by hydrolysis of the diphenylketimine moiety (- N=C - Ph2). The 2-azaallyl anions were synthesized from the reaction of diphenylketimine or N-[aryl-methylene]-α-phenylbenzenemethanamine with potassium bis(trimethylsilyl) amide (KHMDS) in situ and used to initiate the ROP of aziridines leading to well-defined α-(Ph2C=N)-α′-aryl-ω-NH PAzs. Along with the diphenylketimine group (- N=C - Ph2), aryl functionalities, such as pyridine and triphenylphosphine moieties, can also be incorporated to the chain end. Chain extension has been applied for the synthesis of poly(N-sulfonyl aziridine)-block-poly(?-caprolactone) (PAz-b-PCL) block copolymers by utilization of the primary amine end group as initiating sites for the ROP of ?-caprolactone catalyzed by tin 2-ethyl hexanoate (SnOct2). Taking advantage of this synthetic approach, core cross-linked multiarm star (CCS) polymers with an outermost shell having amino and triphenylphosphine functionalities have been synthesized via "arm-first" strategy.

Access to α-Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide

A straightforward and transition-metal-free approach for the efficient synthesis of α-arylglycine derivatives from aromatic imines and carbon dioxide was enabled by an umpolung carboxylation reaction. Various substituted diphenylmethimines underwent the carboxylation smoothly with carbon dioxide in the presence of potassium tert-butoxide and 18-crown-6 to give the corresponding carboxylated products in good to high yields. Besides the enhancement of the solubility of potassium tert-butoxide in THF, 18-crown-6 also plays key roles in suppressing the reverse protonation or 1, 3-proton shift isomerization as well as by stabilizing the carboxylated intermediate.

Sustainable iron-catalyzed direct imine formation by acceptorless dehydrogenative coupling of alcohols with amines

The Acceptorless Dehydrogenative Coupling (ADC) of alcohols with amines is reported using a heterogeneous Fe-catalyst. The reaction operates under mild conditions with the liberation of dihydrogen and water as the byproducts. The developed ADC strategy is simple, efficient, exhibits wide functional group tolerance and can be scaled up. The present catalytic approach possesses a dual role; acting as a catalyst as well as being magnetically separable. The sustainable reuse of a heterogeneous iron catalyst is also shown.

Activation of the Si-B Linkage: Copper-Catalyzed addition of nucleophilic silicon to imines

Activation of the Si-B bond through copper-catalyzed transmetalation quickly developed into a practical method to generate Cu-Si reagents These silicon nucleophiles cleanly add to aldehyde-derived imine electrophiles to form R-silylated amines in protic media, and no carbon-tonitrogen Brook-type rearrangement of the intermediate anion is observed. Aside from electron-withdrawing groups at the imine nitrogen atom, for example, SO2Tol and P(O)Ph2, previously delicate nitrogen substituents such as phenyl or benzhydryl are tolerated. The same protocol also allows the unprecedented addition to representative ketone-derived imines.

Chiral lanthanum(III)-binaphthyldisulfonate complexes for catalytic enantioselective strecker reaction

A catalytic enantioselective Strecker reaction catalyzed by novel chiral lanthanum(III)-binaphthyl disulfonate complexes was developed. The key to promoting the reactions was a semistoichiometric amount of AcOH or i-PrCO2H, which takes advantage of HCN ge

Catalytic asymmetric Strecker hydrocyanation of imines using Yb(OTf) 3-pybox catalysts

We have explored the highly enantioselective Strecker hydrocyanation of a wide range of aromatic, α,β-unsaturated, heterocyclic, and aliphatic aldimines with good to excellent conversions and ees up to 98% in the presence of catalytic amounts of Yb(OTf)s

Asymmetric Strecker reaction of N-benzhydrylimines utilising new tropos biphenyldiol-based ligands

The synthesis of a library of N-arenesulfonyl-1,3-oxazolidinyl-substituted biphenyldiols is presented. A set of two central intermediates together with easily accessible N-arenesulfonylamino alcohols furnish a broad variety of 1,3-oxazolidines. These are applied as chiral tropos ligands in a titanium-mediated Strecker-type reaction of N-benzhydrylimines. A correlation between the ee values in the product and the diastereomeric ratio concerning the chiral axis of the ligand is made. Those substituents in the ligand which proved to lead to a higher preference for one diastereomeric conformer of the chiral axis in related compounds now provide the most selective ligands. Two privileged ligands are identified that afford superior results in 8 of 13 screenings. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Indium triflate catalyzed reaction of diisopropyl diazomethylphosphonate with imines as a new approach to cis- and trans-aziridine-2-phosphonates

A new and efficient synthesis of cis- and trans-aziridine-2-phosphonates by metal-catalyzed aziridination reaction of diisopropyl diazomethylphosphonate and substituted aryl imines is reported. By exploring the influence of different Lewis acids employed as catalysts, imine nitrogen substituents, and the solvent effects we conclude that the best results are obtained when N-diphenylmethyl-substituted benzylimines are reacted with diisopropyl diazomethylphosphonate in methylene chloride at 0 °C in the presence of In(OTf)3 as catalyst.

Synthesis of 1,2-dihydropyridines using vinyloxiranes as masked dienolates in imino-aldol reactions

The application of vinyloxiranes, substituted with an electron-withdrawing group, as masked dienolates in vinylogous imino-aldol reactions was achieved. Under the reaction conditions highly substituted 1,2-dihydropyridines were obtained in moderate to good yields. Mechanistic studies indicate that the reaction proceeds via the formation of an (E)-amino-α,β-unsaturated aldehyde, followed by isomerization to the (Z)-isomer, cyclization, and elimination of a water molecule, leading to the formation of the 1,2-dihydropyridine.