57754-81-1

Usage

InChI:InChI=1/C13H19NO2/c1-4-5-10-16-13(15)11-6-8-12(9-7-11)14(2)3/h6-9H,4-5,10H2,1-3H3

Upstream product

• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 71-36-3 butan-1-ol 
• 201230-82-2 carbon monoxide 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 94-25-7 4-amino-benzoic acid butyl ester 
• 124-38-9 carbon dioxide 
• 96603-18-8 4-(dimethylamino)-N-(2-hydroxyethyl)benzamide 

Relevant academic research and scientific papers

Practical: In situ -generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters

An effective method for alkoxycarbonylation of (hetero)aryl bromides is developed in the presence of in situ-generated phosphinite ligands tBu2POR (R = nBu, nPr, Et or Me). For this purpose commercially available tBu2PCl was used as the pre-ligand in the presence of different alcohols. For the first time cross coupling reactions with two alcohols-one generating the ligand, the other used as substrate-were developed. Through this method, ligand optimization can be performed in a more efficient manner and the desired products could be obtained with good yields and selectivity.

Carbon Dioxide Reduction to Methylamines under Metal-Free Conditions

The first metal-free catalysts are reported for the methylation of amines with carbon dioxide. Proazaphosphatrane superbases prove to be highly active catalysts in the reductive functionalization of CO2, in the presence of hydroboranes. The new methodology enables the methylation of N-H bonds in a wide variety of amines, including secondary amines, with increased chemoselectivity. Organocatalysis: Proazaphosphatrane superbases prove to be highly active catalysts in the reductive functionalization of CO2, in the presence of hydroboranes. The new method makes possible the methylation of N-H bonds in a wide variety of amines, including secondary amines (see picture), with increased chemoselectivity.

Zinc-catalyzed amide cleavage and esterification of β- hydroxyethylamides

Snipping tool: Zn(OTf)2 is an efficient catalyst for selective cleavage of amides bearing a β-hydroxyethyl group on the nitrogen atom. The mechanism involves an N,O-acyl rearrangement and transesterification. This new catalytic system can be applied to sequence-specific peptide bond scission at the amine side of a serine residue. Tf=trifluoromethanesulfonyl. Copyright

Synthesis and catalytic applications of stable palladium dioxygen complexes

The synthesis and characterization of air-stable palladium dioxygen complexes Pd(O2)L2 of basic phosphines L = P(1-Ad) 2nBu, PtBu2nBu is described. Contrary to general belief, these dioxygen complexes are stable catalyst precursors for palladium-catalyzed coupling reactions. Specifically, palladium-catalyzed formylations and alkoxy carbonylations of aryl bromides proceed in high yield in air using commercial non-degassed solvents. It is shown that Pd(O2)L2 complexes are reduced back to the catalytically active palladium(0) species in the reductive atmosphere of CO or H2 at the onset of the carbonylation reaction.

Addition reactions and redox esterifications of carbonyl compounds by N-heterocyclic carbenes of indazole

Thermal decarboxylation converts 1,2-dimethylindazolium-3-carboxylate into indazol-3-ylidene, which reacts in situ with ketones to form stable 1:1 adducts. When the reaction is conducted with aromatic aldehydes in alcohols, redox esterifications to benzoates are observed. Model reactions such as redox esterifications of aromatic aldehydes with sodium alcoholates in the presence of 1,2-dimethylindazolium salt and oxidations of sodium benzylates by 1,2-dimethylindazolium salt to aldehydes lend support to a Cannizzaro-type mechanism of this reaction.

Efficient carbonylation of aryl and heteroaryl bromides using a palladium/diadamantylbutylphosphine catalyst

A general palladium-catalyzed alkoxycarbonylation of aryl and heteroaryl bromides has been developed in the presence of bulky monodentate phosphines. Studies of the butoxycarbonylation of three model substrates revealed the advantages of di-1-adamantyl-n-butylphosphine compared to other ligands. In the presence of this catalyst system various bromoarenes provided the corresponding benzoic acid derivatives (ester, amides, acids) in excellent yield at low catalyst loadings (0.5 mol% Pd or below).

Intramolecular charge transfer dual fluorescence of p- dimethylaminobenzoates

A series of ester, p-N,N-dimethylaminobenzoates ((CH3) 2NC6H4COOR, R=n-CnH2n+1, n=1,2,...,8), were synthesized and their fluorescence spectra were recorded. Intramolecular charge transfer (CT) dual fluorescence was found in common organic solvent or in water with cetyltrimethylammonium bromide (CTAB) micelle. The fluorescence intensity ratio of CT band to normal band (I CT/ILE) was decreased dramatically with the increasing of carbon number of R group when the carbon number of R group were 1-3, but the dependence was not obvious when the carbon number of R group were 4-8. Oppositely, the ICT/ILE was increased with increasing of carbon number of R group in water with CTAB micelle.