3004-58-8

Upstream product

• 10049-90-8 N,N-diethyl-α-hydroxy-α-phenylbenzeneacetamide 
• 1871-76-7 diphenylacetic acid chloride 
• 109-89-7 diethylamine 
• 3699-30-7 potassium diethyldithiocarbamate 
• 21954-69-8 diethyl-amidosulfurous acid methyl ester 
• 117-34-0 2,2-diphenylacetic acid 
• 81838-75-7 N,N-Diethyl-N'-hydroxy-2,2-diphenyl-acetamidine 
• 7647-01-0 hydrogenchloride 
• 685-91-6 diethylacetamide 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 2431-96-1 N,N-diethylphenylacetamide 
• 121-44-8 triethylamine 
• 5411-58-5 ethyl N,N-diethyloxamate 

Downstream Products

• 947-91-1 Diphenylacetaldehyde 
• 78752-20-2 diphenylthioacetic acid diethylamide 
• 119-61-9 benzophenone 
• 124-38-9 carbon dioxide 
• 10049-90-8 N,N-diethyl-α-hydroxy-α-phenylbenzeneacetamide 
• 109-89-7 diethylamine 
• 102894-23-5 2,2-diphenyl-4-piperidino-butyric acid diethylamide 

Relevant academic research and scientific papers

Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2

A novel, in-situ synthesis of dichlorotriphenylphosphorane (Ph3PCl2) is accomplished upon combining PPh3and the easily prepared hypervalent iodine reagent iodobenzene dichloride (PhICl2). The phosphorane is selectively generated in the presence of carboxylic acid or alcohol residues to rapidly produce acyl chlorides and alkyl chlorides in high yields. Addition of EtOH, PhOH, BnOH, Et2NH or CH2N2results in the direct synthesis of esters, amides and diazo ketones from carboxylic acids.

Direct amidation of carboxylic acids with tertiary amines: Amide formation over copper catalysts through C-N bond cleavage

A copper-catalyzed system for the amidation of carboxylic acids with tert-amines through C-N bond cleavage was developed. This protocol is practical and represents a simple way to produce functionalized amides from basic starting materials in moderate to good yields. A plausible mechanism is proposed for the reaction. Copyright

A general and practical palladium-catalyzed direct a-arylation of amides with aryl halides

An efficient system for the direct catalytic intermolecular α-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indolebased phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α-protons of amides (pK a up to 35) were reversibly depotonated by lithium tert-butoxide (LiO-t-Bu), sodium tert-butoxide (NaO-t-Bu) or sodium bis(trimethylsilyl)amide [NaN(SiMe3)2].

Palladium-catalyzed direct intermolecular α-arylation of amides with aryl chlorides

An efficient catalytic system for the direct intermolecular α-arylation of acetamide derivatives with aryl chlorides is presented. Chemoselectivities up to 10:1 in the mono-and diarylation of acetamides were achieved by careful selection of bases, solvent

A mild titanium-based system for the reduction of amides to aldehydes

A mild method for the reduction of amides to aldehydes using 1,1,3,3-tetramethyldisiloxane/titanium(IV) isopropoxide reducing system is described. The reaction occurs under mild conditions and allows the reduction of aromatic as well as aliphatic, tertiary amides to the corresponding aldehydes, in good yields. This methodology was extended to the reduction of aromatic secondary and primary amides to the corresponding aldehydes.

The conversion of carboxylic acids into amides via NCS/triphenylphosphine

Amides can be generated in very high yields under mild conditions from the corresponding carboxylic acid and amine in the presence of equivalent amounts of triphenylphosphine and N-halosuccinimides, e.g., NCS or NBS.