5461-52-9

Upstream product

• 109-89-7 diethylamine 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2043-61-0 cyclohexanecarbaldehyde 
• 3768-61-4 N,N,N',N'-tetraethylthioamine 
• 105398-69-4 Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 
• 24398-21-8 N,N-Diethyl-p-chlorbenzolsulfenamid 
• 24398-43-4 N,N-diethyl-S-2-nitrobenzenesulfenamide 
• 221887-36-1 2,2,2-tribromoethyl cyclohexanecarboxylate 
• 931-51-1 cyclohexylmagnesiumchloride 
• 626-62-0 Cyclohexyl iodide 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 74-85-1 ethene 
• 1122-56-1 cyclohexylcarboxamide 

Downstream Products

• 90150-05-3 N,N-diethyl-cyclohexylmethylamine 
• 100-49-2 cyclohexylmethyl alcohol 
• 101874-45-7 diethyl-(1-cyclohexyl-2-phenyl-ethyl)-amine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 75115-53-6 (1-chloro-cyclohexyldimethyl)diethylamine 

Relevant academic research and scientific papers

Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis

A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.

Hydroamination of unactivated alkenes catalyzed by novel platinum(II) N -heterocyclic carbene complexes

Cationic platinum(II) complexes with bi- or tridentate (pincer) functionalized NHC ligands were found to be catalytically active in the hydroamination of unactivated alkenes. In some cases, the presence of water had an activating effect on the complexes. Reactions with the N-nucleophilic substrate morpholine led to a noncatalytic reaction in which the deprotonation product of the key cationic β-aminoalkyl platinum complex could be isolated and characterized. Surprisingly, attempted protonation of this complex did not give the expected N-alkylated product, indicating either the thermodynamic unfavorability of C-Pt bond cleavage or its kinetic inertness.

Synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using [Et 2NSF2]BF4 as a practical cyclodehydration agent

The preparation of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using XtalFluor-E ([Et2NSF2]BF4) as cyclodehydration reagent is described. Various functionalized 1,3,4-oxadiazoles were synthesized and it was found that the use of acetic acid as an additive generally improved the yields.

Atom transfer carbonylation using ionic liquids as reaction media

Photo-induced ATC reactions of RI, CO, and amines to produce amides, were examined using ionic liquids, such as [bmim]PF6 and [bmim]NTf2, as reaction media in the presence of a catalytic amount of a Pd-carbene complex. When the primary alkyl iodide was used, the yield of the amide was lowered due to competing SN2 reactions between RI and amines, whereas the reaction of the tertiary alkyl iodides was dependent on the structure of the substrates. ATC reactions of a wide variety of secondary RI proceeded smoothly when ionic liquids were used as reaction media. The Pd-catalyst and ionic liquid could also be recycled.

Cross-coupling reactions of carbamoyl chlorides and Grignard reagents: A new rapid synthesis of tertiary amides

Tributyl phosphine or nickel catalysts allow the cross-coupling reaction between N,N-dialkylcarbamoyl chlorides and alkyl or aryl Grignard reagents. This convenient and simple method affords tertiary amides with moderate to excellent yields in short reaction times. (C) 2000 Elsevier Science Ltd.

Direct transacylation of 2,2,2-trihaloethyl esters with amines and alcohols using phosphorus(III) reagents for reductive fragmentation and in situ activation

Amides and esters have been synthesized from 2,2,2-trihaloethyl esters in one pot using phosphorus(III) reagents as reductants, with resultant carboxylate activation as an acyloxyphosphonium intermediate, and in situ trapping by amine or alcohol nucleophiles. Secondary and tertiary amides were synthesized, including a dipeptide, in good yields using hexamethylphosphorous triamide, (Me2N)3P, as reducing agent. Optimal yields of esters derived from primary and secondary alcohols were obtained using tributylphosphine and DMAP. Tribromoethyl esters provided yields superior to those obtained with trichloroethyl esters.

A direct and mild conversion of tertiary aryl amides to methyl esters using trimethyloxonium tetrafluoroborate: A very useful complement to directed metalation reactions

The scope and generality of a direct process for the conversion of tertiary amides directly to methyl esters has been investigated. The process involves a two-step, one pot procedure in which a tertiary amide is first treated with trimethyloxonium tetrafluoroborate to generate an imidate intermediate which is then hydrolyzed, generally by the addition of saturated aqueous sodium bicarbonate solution. Although this process fails for aliphatic amides, very good yields are realized for a variety of amides derived from aromatic carboxylic acids. Steric hindrance at the N-alkyl group is well tolerated; thus N,N-dimethyl, -diethyl, and -diisopropyl amides can all be utilized successfully. (C) 2000 Elsevier Science Ltd.

New reactions of the thiocarbonyl function. The synthesis of hindered peptides

The well-known radical chemistry of the thiocarbonyl function has been expanded to include the concerted reaction between an O-acyl derivative of N-hydroxypyridine-2(1H)-thione (a Barton PTOC ester) and a sulfenamide. The atom-economical process spawned a carboxamide and an unsymmetrical disulfide of synthetic and biological value. The reaction was successfully applied to the synthesis of sterically encumbered, urethane-protected dipeptides. The oxidation-reduction technology pertaining to the disulfide-phosphine combination facilitated the generation of transient Barton PTOC esters. In conjunction with the appropriate benzenesulfenamide, the Barton PTOC ester of benzoyl-L-leucine was shown to preserve optical integrity according to the sensitive Young test, albeit at low temperature. However, the thermodynamic forces at play are powerful and, as a result, the yields were not compromised. In all but the sterically demanding instances, the parent free amine almost matched the reaction time, yield, and enantiomeric excess of the corresponding benzenesulfenamide in its reaction with a Barton PTOC ester.

N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides

The reaction between an acyl derivative of N-hydroxypyridine-2(1H)- thione (a Barton PTOC ester) and either an amine (primary or secondary), or the corresponding sulfenamide, led to the formation of a carboxamide in a clean transformation requiring minimal work-up and purification. The reaction with a sulfenamide is particularly useful since the only by-product, an unsymmetrical disulfide, is of both synthetic and biological value. In sterically demanding cases, Barton PTOC esters were more reactive towards benzenesulfenamides than to the corresponding free amines.