14288-22-3

Upstream product

• 4285-42-1 N-phenyl-N-methylcarbamoyl chloride 
• 79-37-8 oxalyl dichloride 
• 100-61-8 N-methylaniline 
• 3155-16-6 diphenyl oxalate 
• 2621-79-6 ethyl N-methyl-N-phenylcarbamate 
• 201230-82-2 carbon monoxide 
• 100-39-0 benzyl bromide 
• 591-50-4 iodobenzene 
• 124-41-4 sodium methylate 
• 60-29-7 diethyl ether 

Downstream Products

• 61110-50-7 N-methyl-N-phenyl-2-oxopropanamide 
• 7025-95-8 N,N'-dimethyl-N,N'-diphenylethylenediamine 
• 66661-54-9 N,N'-Bis-chloromethyl-N,N'-diphenyl-oxalamide 

Relevant academic research and scientific papers

Reagent Design and Ligand Evolution for the Development of a Mild Copper-Catalyzed Hydroxylation Reaction

Parallel synthesis and mass-directed purification of a modular ligand library, high-throughput experimentation, and rational ligand evolution have led to a novel copper catalyst for the synthesis of phenols with a traceless hydroxide surrogate. The mild reaction conditions reported here enable the late-stage synthesis of numerous complex, druglike phenols.

A convenient one-pot synthesis of symmetric secondary and tertiary vicinal diamines

A convenient one-pot synthesis of symmetric vicinal diamines utilizing sodium borohydride/trifluoroacetic acid reduction methodology is described.

N,N-DISUBSTITUTED LITHIUM BIS(CARBAMOYL)CUPRATE. A CONVENIENT COMPLEX FOR ONE-POT CONVERSIONS OF AMINES TO FORMAMIDES, OXAMIDES, CARBAMATES, AND OXAMIC ACIDS

Lithium bis(carbamoyl)cuprates (2) were readily derived from secondary amines such as N-methylaniline, N-methylbenzylamine, and diethylamine, under mild carbonylation conditions (0 deg C, 1 atm of carbon monoxide), but diphenylamine and benzylphenylamine were unsuitable as the starting materials.The carbamoylcopper complexes 2 formed in ether were readily converted to the corresponding formamides, oxamides, carbamates, and oxamic acids by the appropriate treatment.The formation and stability of 2 depended much on the solvent used.The higher polarity effect of the solvent (DME, THF, and HMPA) made 2 less stable and caused concomitant evolution of carbon monoxide in further reactions.A palladium catalyst was found to be effective for cross-coupling reactions of 2 with iodobenzene or (E)-β-bromostyrene.

Carbamoylation using the CO-containing Copper Complex derived from Lithium N-methylanilide

Lithium N-methylanilide, prepared from N-methylaniline and n-butyllithium, readily absorbed CO at atmospheric pressure in the presence of cuprous iodide to produce a CO-containing copper complex.Treatment of this complex with organic halides gave the corresponding amides in good yields.Keywords - carbonylation; carbamoylation; carbon monoxide; cuprous iodide; lithium N-methylanilide