68003-55-4

Upstream product

• 100-52-7 benzaldehyde 
• 107-11-9 1-amino-2-propene 
• 146039-11-4 Allyl-phosphorimidic acid triethyl ester 
• 13716-45-5 diethyl trimethylsilyl phosphite 
• 19807-41-1 chlorophenylcarbene 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 10017-11-5 allylammonium chloride 
• 106-95-6 allyl bromide 
• 622-79-7 benzyl azide 
• 4383-22-6 Allylbenzylamine 
• 3376-23-6 C-phenyl-N-methylnitrone 
• 100-51-6 benzyl alcohol 
• 92-29-5 (E,E)-1,3,5-triphenyl-2,4-diazapenta-1,4-diene 
• 124948-53-4 N-Benzyliden-2-hydroxy-1-propanamin 

Downstream Products

• 37932-67-5 1-allyl-5-phenyl-imidazolidine-2,4-dione 
• 188818-01-1 N-benzylidene-2,3-dibromopropylamine 
• 30312-51-7 1-benzyl-2-propyl-1.2-azaborolane 
• 30312-50-6 1-benzyl-2-iso-butyl-1.2-azaborolane 
• 627-37-2 N-methyl-N-allylamine 
• 4383-22-6 Allylbenzylamine 
• 31201-91-9 4-methyl-1-phenyl-2-aza-1,3-butadiene 
• 219517-92-7 (R,S)-N,N'-diallyl-1,2-diphenyl-1,2-ethylenediamine 
• 100-52-7 benzaldehyde 
• 86926-55-8 phenyl(prop-2-en-1-ylamino)acetonitrile 
• 142301-65-3 N-Allyl-N-benzyltrifluoroacetamide 

Relevant academic research and scientific papers

Easy access to N,N-Bis(but-3-enyl)-, N-Allyl-N-(but-3-enyl)-, and N-(but-3-ynyl)-N-(but-3-enyl)-amines

N,N-Bis(but-3-enyl)amines 5a-i were prepared in overall 74% yield from 1-(triphenylphosphoroylideneaminoalkyl)benzotriazole using an aza-Wittig reaction with aldehydes followed by a double Grignard reaction with allylmagnesium bromide. Use of vinyl or 1-propynylmagnesium bromide and allylmagnesium bromide in a sequential fashion also formed the expected doubly unsaturated amines 9a,b and 12, respectively.

Retro-Cope Eliminations in the Synthesis of 1,2,5-Oxadiazinanes from Allylamines and Nitrones: a Method for the Amination of Unactivated Alkenes

Heating an allylamine (e.g. 9) and a nitrone (e.g. 10) in an inert solvent produces often excellent yields of a 1,2,5-oxadiazinane (e.g. 11) by a pathway which features a retro-Cope elimination and a Meisenheimer rearrangement; reduction of the oxadiazina

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys

HCN on Tap: On-Demand Continuous Production of Anhydrous HCN for Organic Synthesis

A continuous process for the on-demand generation, separation, and reaction of hydrogen cyanide (HCN) using membrane separation technology was developed. The inner tube of the reactor is manufactured from a gas-permeable, hydrophobic fluoropolymer (Teflon AF-2400) membrane. HCN is formed from aqueous reagents within the inner tube and then diffuses through the membrane into an outer tubing containing organic solvent. This technique enabled the safe handling of HCN for three different organic transformations without the need for distillation.

Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis

Primary aminoboranes (RNHBR2), which are readily available by spontaneous dehydrocoupling of amines and boranes cleanly react at room temperature with aldehydes to give aldimines. The overall transformation from amines to aldimines can be conveniently performed by a sequential one-pot reaction. This synthetic strategy is especially useful for electron poor and bulky amines which are reluctant to react with aldehydes under dehydration conditions. Using a Glorius robustness screen, we show that this methodology is chemoselective, and functional group tolerant. Computational and experimental data support the irreversible formation of the aldimine product in marked contrast with traditional methods.

Cobalt-Catalyzed α-Arylation of Substituted α-Halogeno β-Lactams

The treatment of 3-bromo β-lactams by an aryl Grignard, in the presence of CoCl2 (2 mol %) and TMEDA (2 mol %) in THF, produces 3-aryl β-lactams in good yields and excellent diastereoselectivity.

Synthesis of Cyclic N-Hydroxylated Ureas and Oxazolidinone Oximes Enabled by Chemoselective Iodine(III)-Mediated Radical or Cationic Cyclizations of Unsaturated N-Alkoxyureas

In this study we describe the reactivity of unsaturated N-alkoxyureas in the presence of different combinations of a hypervalent iodine(III) reagent and a bromide source or TEMPO. Three complementary cyclizations can be achieved depending on the reaction conditions. On the one hand, PIFA with pyridinium bromide leads to an oxybromination reaction. On the other hand, bis(tert-butylcarbonyloxy)iodobenzene with tetrabutylammonium bromide or TEMPO triggers aminobromination or aminooxyamination reactions, respectively. Control experiments showed that the three reactions proceed through distinct mechanisms: the first process is ionic while the other two follow a radical manifold. (Figure presented.).

Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades

The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.

Iron-Catalyzed Reductive Ethylation of Imines with Ethanol

The borrowing hydrogen strategy has been applied to the ethylation of imines with an air-stable iron complex as precatalyst. This approach opens new perspectives in this area as it enables the synthesis of unsymmetric tertiary amines from readily available substrates and ethanol as a C2 building block. A variety of imines bearing electron-rich aryl or alkyl groups at the nitrogen atom could be efficiently reductively alkylated without the need for molecular hydrogen. The mechanism of this reaction, which shows complete selectivity for ethanol over other alcohols, has been studied experimentally and by means of DFT computations.

Preparation of homoallylic amines via a three-component coupling process

A three-component synthesis of homoallylic amines is described. The allylboronic species were generated in situ by homologation of vinyl boroxines with trimethylsilyldiazomethane, then followed by trapping of the allylboron intermediate with imines. Twenty-seven compounds were successfully prepared in moderate to high yields. Imines bearing various functional groups were tolerated, including aliphatic, aromatic and heteroaromatic substituents. Further elaboration of some of the homoallylic amines to form azeditines is also reported.