62740-72-1

Upstream product

• 109-72-8 n-butyllithium 
• 538-51-2 benzylidene phenylamine 
• 109-69-3 n-Butyl chloride 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 6630-33-7 ortho-bromobenzaldehyde 
• 62-53-3 aniline 
• 1009-14-9 phenyl butyl ketone 
• 77821-54-6 Phenyl-[1-phenyl-pent-(Z)-ylidene]-amine 
• 5384-63-4 1,1-diphenylpentanol 
• 109-52-4 valeric acid 
• 624-24-8 methyl valerate 
• 32347-03-8 N-(2-bromobenzylidene)aniline 
• 2325-27-1 N-phenyltriphenyliminophosphorane 
• 622-37-7 Phenyl azide 

Relevant academic research and scientific papers

Iron-catalysed 1,2-aryl migration of tertiary azides

1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.

Lithium–Bromide Exchange versus Nucleophilic Addition of Schiff's base: Unprecedented Tandem Cyclisation Pathways

By exploring lithium–bromide exchange reactivity of aromatic Schiff's bases with tert-butyllithium (tBuLi), we have revealed unprecedented competitive intermolecular and intramolecular cascade annulation pathways, leading to valuable compounds, such as iso-indolinones and N-substituted anthracene derivatives. A series of reaction parameters were probed, including solvent, stoichiometry, sterics and organolithium reagent choice, in order to understand the influences that limit such ring-closing pathways. With two viable reactivity options for the organolithium on the imine; namely, nucleophilic addition or lithium–bromide exchange, a surprising competitive nature was observed, where nucleophilic addition dominated, even under cryogenic conditions. Considering the most commonly used solvents for lithium–bromide exchange, tetrahydrofuran (THF) and diethyl ether (Et2O), contrasting reactivity outcomes were revealed with nucleophilic addition promoted in THF, while Et2O yielded almost double the conversion of cyclic products than in THF.

Unprecedented Nucleophilic Additions of Highly Polar Organometallic Compounds to Imines and Nitriles Using Water as a Non-Innocent Reaction Medium

In contrast to classic methods carried out under inert atmospheres with dry volatile organic solvents and often low temperatures, the addition of highly polar organometallic compounds to non-activated imines and nitriles proceeds quickly, efficiently, and chemoselectively with a broad range of substrates at room temperature and under air with water as the only reaction medium. Secondary amines and tertiary carbinamines are furnished in yields of up to and over 99 %. The significant solvent D/H isotope effect observed for the on-water nucleophilic additions of organolithium compounds to imines suggests that the on-water catalysis arises from proton transfer across the organic–water interface. The strong intermolecular hydrogen bonds between water molecules may play a key role in disfavoring protonolysis, which occurs extensively in other protic media such as methanol. This work lays the foundation for reshaping many fundamental s-block metal-mediated organic transformations in water.

Exploiting Deep Eutectic Solvents and Organolithium Reagent Partnerships: Chemoselective Ultrafast Addition to Imines and Quinolines Under Aerobic Ambient Temperature Conditions

Shattering the long-held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non-activated imines and quinolines has been accomplished in green, b

Development of highly enantioselective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile

l-Pipecolinic acid derived N-formamides have been developed as new Lewis basic organocatalysts that promote the asymmetric reduction of N-aryl ketimines using trichlorosilane as the reducing agent. The substituent on N4 of the piperazinyl backbone and the

Novel one-pot synthesis of N-alkyl arylamines from oxime ethers using organometallic reagents

A novel one-pot synthesis of α,α-disubstituted secondary arylamines from oxime ethers has been developed by two separate additions of organometallic reagents. As a related arylamine construction, very efficient synthesis of N-(diallyl)methyl arylamines is

L-piperazine-2-carboxylic acid derived N-formamide as a highly enantioselective Lewis basic catalyst for hydrosilylation of N-aryl imines with an unprecedented substrate profile

L-Piperazine-2-carboxylic acid derived N-formamides have been developed as highly enantioselective Lewis basic catalysts for the hydrosilylation of N-aryl imines with trichlorosilane. The arene sulfonyl group on N4 was found to be critical for the high en

Highly efficient alkylation to ketones and aldimines with Grignard reagents catalyzed by zinc(II) chloride

A highly efficient alkylation to ketones and aldimines with Grignard reagents in the presence of catalytic trialkylzinc(II) ate complexes derived from ZnCl2 (10 mol %) in situ was developed. This simple Zn(II)-catalyzed alkylation could minimize the well-known but serious problems with the use of only Grignard reagents, which leads to reduction and aldol side products, and the yield of desired alkylation products could be improved. Copyright

Regio- and stereoselective double alkylation of β-enamino esters with organolithium reagents followed by one-pot reduction: convenient method for the synthesis of tertiary γ-amino alcohols

An easy, high yielding and stereoselective procedure for the preparation of tertiary γ-amino alcohols starting from β-enamino esters is presented. In this procedure, the double alkylation of β-enamino esters with organolithium reagents is followed by one-

Novel domino elimination-rearrangement-addition reaction of N-alkoxy(arylmethyl)amines to N-alkyl arylamines

A new domino reaction of N-alkoxy(arylmethyl)amines to N-alkyl arylamines, consisting of three types of reactions: elimination of alcohol, rearrangement of the aryl group, and addition of an organolithium or a magnesium reagent, has been developed for the first time. Georg Thieme Verlag Stuttgart.