128037-34-3

Upstream product

• 134636-41-2 N-Butyl-cyclohexanecarboximidic acid 2-thioxo-2H-pyridin-1-yl ester 
• 75-66-1 2-methylpropan-2-thiol 
• 109-73-9 N-butylamine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 24398-46-7 2-nitro-benzenesulfenic acid butylamide 
• 105398-69-4 Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 
• 221887-36-1 2,2,2-tribromoethyl cyclohexanecarboxylate 
• 111-36-4 n-butyl isocyanide 
• 98-89-5 Cyclohexanecarboxylic acid 
• 626-62-0 Cyclohexyl iodide 
• 13939-06-5 molybdenum hexacarbonyl 
• 201230-82-2 carbon monoxide 
• 1119-03-5 N-Butyl-carbamidsaeure-allylester 
• 10500-30-8 cyclohexanoyl bromide 

Downstream Products

• 128037-35-4 N-Butyl-N-cyclohexanecarbonyl-3-acetoxy-2,2-dimethylpropanamide 
• 1448773-57-6 diethyl ((butylamino)(cyclohexyl)methyl)phosphonate 
• 134636-41-2 N-Butyl-cyclohexanecarboximidic acid 2-thioxo-2H-pyridin-1-yl ester 
• 98-89-5 Cyclohexanecarboxylic acid 
• 142-62-1 hexanoic acid 
• 149817-40-3 N-Butyl-cyclohexanecarboximidoyl chloride 

Relevant academic research and scientific papers

Low-Pressure Radical11C-Aminocarbonylation of Alkyl Iodides through Thermal Initiation

A radical11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated11C-aminocarbonylation, which is limited to the preparation of11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.

Synthesis of Aliphatic Amides through a Photoredox Catalyzed Radical Carbonylation Involving Organosilicates as Alkyl Radical Precursors

Alkyl radicals, from primary to tertiary, formed by photocatalyzed oxidation of organosilicates, are involved efficiently in radical carbonylation with carbon monoxide (CO), in the presence of various amines and CCl4, leading to a variety of amides in moderate to good yields. (Figure presented.).

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.

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

Convenient metal-free direct oxidative amidation of aldehyde using dibromoisocyanuric acid under mild conditions

A facile method for the direct synthesis of amides from aldehydes is described. Amide bonds were synthesized by an oxidative amidation in the presence of dibromoisocyanuric acid (DBI). Treatment of aromatic and aliphatic aldehydes with dibromoisocyanuric acid generated acyl bromide intermediates, which were employed to react with a variety of secondary and primary amines to give amides. Through this reaction method, various amides were synthesized directly from aldehydes under mild conditions in high yields and short times. This facile and efficient procedure provides potential strategy for the direct synthesis of amides from aldehydes.

Nickel-catalyzed dehydrogenative cross-coupling: Direct transformation of aldehydes into esters and amides

By exploring a new mode of nickel-catalyzed cross-coupling, a method to directly transform both aromatic and aliphatic aldehydes into either esters or amides has been developed. The success of this oxidative coupling depends on the appropriate choice of catalyst and organic oxidant, including the use of either α,α,α-trifluoroacetophenone or excess aldehyde. Mechanistic data that supports a catalytic cycle involving oxidative addition into the aldehyde C-H bond is also presented.

Light-enabled synthesis of anhydrides and amides

Recently, we have demonstrated that the photogeneration of Vilsmeier-Haack reagents is possible using only dimethylformamide (DMF) and tetrabromomethane (CBr4) in the bromination of alcohols. Extending these findings to carboxylic acid substrates has produced a mild and facile approach to the in situ formation of symmetric anhydrides, which were conveniently converted to amide derivatives in a one-pot process. The efficient protocols discussed herein are marked by use of UVA LEDs (365 nm), which have reduced the reaction times and come with a low setup cost.

Cyclic guanidine organic catalysts: What is magic about triazabicyclodecene?

(Chemical Equation Presented) The bicyclic guanidine 1,5,7- triazabicyclo[4.4.0]dec-5-ene (TBD) is an effective organocatalyst for the formation of amides from esters and primary amines. Mechanistic and kinetic investigations support a nucleophilic mechanism where TBD reacts reversibly with esters to generate an acyl-TBD intermediate that acylates amines to generate the amides. Comparative investigations of the analogous bicyclic guanidine 1,4,6-triazabicyclo[3.3.0]oct-4-ene (TBO) reveal it to be a much less active acylation catalyst than TBD. Theoretical and mechanistic studies imply that the higher reactivity of TBD is a consequence of both its higher basicity and nucleophilicity than TBO as well as the high reactivity of the acyl-TBD intermediate, which is sterically prevented from adopting a planar amide structure.

Pd-catalyzed oxidative amidation of aldehydes with hydrogen peroxide

Using hydrogen peroxide as a key oxidant, catalytic oxidative amidation between aldehydes and amines was effectively carried out with PdCl2-xantophos as a catalyst in methanol under acidic conditions. The new protocol is mechanistically different from the previous one through β-hydride elimination.

Oxidative amidation of aldehydes and alcohols with primary amines catalyzed by KI-TBHP

Oxidative amidation of aldehydes and alcohols with amines to afford the corresponding amides in excellent yields and ee values over 98% is achieved by using a catalytic amount of KI in combination with TBHP as the external oxidant. This method avoids the use of expensive and/or air-sensitive reagents. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.