2948-37-0

Usage

InChI:InChI=1/C13H12ClN/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,15H,10H2

Upstream product

• 100-44-7 benzyl chloride 
• 106-47-8 4-chloro-aniline 
• 2785-29-7 benzyl potassium 
• 780-21-2 N-(4-chlorobenzylidene)aniline 
• 128965-92-4 N-Benzyl-2-(4-chloro-phenoxy)-2-methyl-propionamide 
• 100-51-6 benzyl alcohol 
• 3296-05-7 1-azido-4-chlorobenzene 
• 108-88-3 toluene 
• 33558-22-4 4-chloro-N-benzylformanilide 
• 100-52-7 benzaldehyde 
• 3459-92-5 DBC 
• 637-87-6 1-Chloro-4-iodobenzene 
• 100-46-9 benzylamine 
• 1613-89-4 (E)-N-benzylidene-4-chloroaniline 

Downstream Products

• 102473-74-5 benzyl-(4-chloro-phenyl)-carbamic acid-(2-diisopropylamino-ethyl ester) 
• 102173-26-2 6-chloro-N-benzyl-1,2,3,4-tetrahydrocarbazole 
• 2215-50-1 N-Benzyl-N-(4-chlor-phenyl)-carbamoylchlorid 
• 104501-73-7 N-Benzyl-N-(4-chloro-phenyl)-S-trimethylsilanylethynyl-thiohydroxylamine 
• 119592-14-2 [3-[Benzyl-(4-chloro-phenyl)-amino]-2-(methoxycarbonyl-hydrazono)-propyl]-phosphonic acid diethyl ester 
• 119591-96-7 [1-[Benzyl-(4-chloro-phenyl)-amino]-2-(methoxycarbonyl-hydrazono)-propyl]-phosphonic acid diethyl ester 
• 19865-58-8 N-(4-chlorophenyl)-α-phenylnitrone 
• 100-52-7 benzaldehyde 
• 780-21-2 N-(4-chlorobenzylidene)aniline 
• 157584-43-5 N-Benzyl-N-(4-chloro-phenyl)-2,2,2-trifluoro-acetamide 
• 157584-46-8 N-Benzyl-N-(4-chloro-phenyl)-2,2,3,3,4,4,4-heptafluoro-butyramide 
• 62336-71-4 2-Benzylamino-5-chlordiphenylselenid 
• 143490-31-7 Benzyl-(4-chloro-phenyl)-dithiocarbamic acid methyl ester 
• 92435-84-2 N-benzyl-4-(chloro)chloroacetanilide 

Relevant academic research and scientific papers

Hydrogen-bonding catalysis of sulfonium salts

Although quaternary ammonium and phosphonium salts are known as important catalysts in phase-transfer catalysis, the catalytic ability of tertiary sulfonium salts has not yet been well demonstrated. Herein, we demonstrate the catalytic ability of trialkyl

Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols

A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.

Platinum Assisted Tandem P–C Bond Cleavage and P–N Bond Formation in Amide Functionalized Bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o: Synthesis, Mechanistic, and Catalytic Studies

The reactions of amide functionalized bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o (1) with platinum salts are described. Treatment of 1 with [Pt(COD)Cl2] yielded a chelate complex, [PtCl2{o-Ph2PC6H4C(O)N(H)C6H4PPh2-o}κ2-P,P] (2), which on subsequent treatment with LiHMDS formed a novel 1,2-azaphospholene-phosphine complex [Pt(C6H5)Cl{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (3) involving a tandem P–C bond cleavage and P–N bond formation. The same complex 3 on passing dry HCl gas afforded the dichloro complex [PtCl2{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (5). Complex 2 upon refluxing in toluene or treatment of 1 with [Pt(COD)Cl2] in the presence of a base at room temperature resulted in the pincer complex [PtCl{o-Ph2PC6H4C(O)N(C6H4PPh2-o)}κ3-P,N,P] (4). Reaction of 1 with [Pt(COD)ClMe] at room temperature also afforded the pincer complex [PtMe{o-Ph2PC6H4C(O)N(C6H4PPh2-o)}κ3-P,N,P] (6). Mechanistic studies on 1,2-azaphospholene formation showed the reductive elimination of LiCl to form a phosphonium salt that readily adds one of the P–C bonds oxidatively to the in situ generated Pt0 species to form a chelate complex 3. The analogous palladium complex [PdCl2{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (7) showed excellent catalytic activity toward N-alkylation of amines with alcohols with a very low catalyst loading (0.05 mol %), and the methodology is very efficient toward the gram-scale synthesis of many N-alkylated amines.

Reduction of imines with a reusable bimetallic PdCo-Fe3O4catalyst at room temperature under atmospheric pressure of H2

Bimetallic nanocatalysts have been used for the development of organic reactions, owing to the synergistic effect between the transition metals. A new procedure for synthesizing amines by the reduction of imines with H2 at atmospheric pressure and room te

Copper(i)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphites

Intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphite diesters proceeded in the presence of Cu(i)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.

[(PPh3)2NiCl2]-Catalyzed C-N bond formation reaction via borrowing hydrogen strategy: Access to diverse secondary amines and quinolines

Commercially available [(PPh3)2NiCl2] was found to be an efficient catalyst for the mono-N-alkylation of (hetero)- A romatic amines, employing alcohols to deliver diverse secondary amines, including the drug intermediates chloropyramine (5b) and mepyramine (5c), in excellent yields (up to 97%) via the borrowing hydrogen strategy. This method shows a superior activity (TON up to 10000) with a broad substrate scope at a low catalyst loading of 1 mol % and a short reaction time. Further, this strategy is also successful in accessing various quinoline derivatives following the acceptorless dehydrogenation pathway.

Cooperative catalysis of molybdenum with organocatalysts for distribution of products between amines and imines

Multi-amino groups and nitrogen donors compound was discovered as an organocatalyst for N-alkylation of alcohols with amines in the presence of Mo(CO)6. The Mo(CO)6/organocatalyst binary system has shown to be a highly active catalyst for the N-alkylation reaction between alcohols and amines with excellent tolerance of variable starting materials bearing different functional groups. Of particular note, this method possessing a superiority selectivity in the synthesis of N-alkylated amines or imines, which can be controlled by the reaction temperature. The cooperative catalysis mechanism in combination of Mo(CO)6 with organocatalyst was elucidated by control experiments.

Synthesis of NHC-Iridium(III) Complexes Based on N-Iminoimidazolium Ylides and Their Use for the Amine Alkylation by Borrowing Hydrogen Catalysis

Anionic NHC ligands recently developed in our group, derived from N-iminoimidazolium ylides, were used to synthesize NHC-iridium(III) complexes. Their catalytic activities were evaluated in the amine alkylation of anilines using borrowing hydrogen catalysis. The high-yielding synthesis of a small library of complexes allowed a rapid screening of the ideal steric bulk of the NHC unit and basicity of the anionic tether for the investigated model reaction. A bulky aromatic N group on the imidazolidene moiety is required to achieve high catalytic activity, and the latter is proportional to the basicity of the anionic group. A selected substrate scope of the reaction was performed, providing fair to excellent yields of the desired alkylated anilines.

Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols

A series of air-stable N-heterocyclic carbene (NHC) Ir(III) complexes (Ir1-6), bearing various combinations of chlorine, pyridine and NHC ligands, were assayed for the N-alkylation of amines with alcohols. It was found that Ir3, with two monodentate 1,3-bis-methyl-imidazolylidene (IMe) ligands, emerged as the most active complex. A large variety of amines and primary alcohols were efficiently converted into mono-N-alkylated amines in 53–96% yields. As a special highlight, for the challenging MeOH, selective N-monomethylation could be achieved using KOH as a base under an air atmosphere. Moreover, this catalytic system was successfully applied to the gram-scale synthesis of some valuable compounds.