34906-86-0

Upstream product

• 5411-58-5 ethyl N,N-diethyloxamate 
• 25726-04-9 phenylglyoxylyl chloride 
• 109-89-7 diethylamine 
• 98-88-4 benzoyl chloride 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 1074-12-0 phenylglyoxal hydrate 
• 4231-26-9 diethylamino-1 phenyl-2 acetylene 
• 201230-82-2 carbon monoxide 
• 108-90-7 chlorobenzene 
• 38078-09-0 diethylamino-sulfur trifluoride 
• 611-73-4 Benzoylformic acid 
• 12082-03-0 tricarbonyl(η6-chlorobenzene)chromium 
• 591-50-4 iodobenzene 
• 617-84-5 N-formyldiethylamine 

Downstream Products

• 4249-64-3 2-diethylamino-1-phenyl-1-ethanol 
• 138835-07-1 cis-3-ethyl-2-methyl-5-phenyloxazolidin-4-one 
• 138835-06-0 trans-3-ethyl-2-methyl-5-phenyloxazolidin-4-one 
• 2019-69-4 N,N-diethyl-2-(2-hydroxyphenyl)acetamide 
• 611-73-4 Benzoylformic acid 
• 64201-10-1 3-ethyl-2-methyl-5-phenyl-oxazolidin-4-one 

Relevant academic research and scientific papers

One-pot route to new α,α-difluoroamides and α-ketoamides

New α,α-difluoroamides (4a-d, 6a-d) and α-ketoamides (5a-d, 7a-d) result from one-pot reactions of α-ketoacids, RCOCO2H (R = C6H5, CH3, CH3CH2, thienyl) (1a-d) with bis(2-methoxyethyl)aminosulfur trifluoride [(CH3-OCH2CH2)2NSF3] (2) (Deoxofluor) or diethylaminosulfur trifluoride [(CH3CH2)2NSF3)] (3) (DAST). Product yields depend on reaction times and the ratio of reagents used. Longer reaction times (～36 h) with a 1:2 ratio of α-ketoacids and 2 or 3 gave major yields of the α,α-difluoroamides, and shorter reaction times (～1 h) produced α,α-ketoamides as the major products. Reactants in a 1:1 ratio resulted in α-ketoamides only.

Ligand-free Zn-catalyzed double carbonylation of aryl iodides with secondary amines: A simple and efficient approach to access α-ketoamides

Herein, we report a Zinc catalyzed double carbonylation of aryl iodides with secondary amines under CO pressure for the synthesis of α-ketoamides in good to excellent yields. This methodology provides a simple and economic approach to derivatize useful α-

Pd-Catalyst Containing a Hemilabile P,C-Hybrid Ligand in Amino Dicarbonylation of Aryl Halides for Synthesis of α-Ketoamides

The amino dicarbonylation of aryl halides affording α-ketoamides with Pd catalysts is highly dependent on the stereoelectronic properties of the involved ligands. Ionic diphosphine ligand L4 can serve as precursor of a hemilabile P,C (phosphine, carbene)-hybrid ligand to form a stable Pd(II)-complex, Pd-L4. In contrast, analogues L1-L3 with a similar 1-(thiophen-3-yl)-benzimidazolyl skeleton behave as typical (mono/di)phosphines. The catalytic system resulting from the complexation of PdCl2(MeCN)2 and L4 exhibits good catalytic performance in terms of aryl iodides conversion (81-95%) and α-ketoamide selectivity (80-91%), as well as the available recyclability in the RTIL of [Bpy]BF4. The in situ FT-IR analysis reveals that the PdCl2(MeCN)2-L4 catalytic system favors the amino dicarbonylation toward α-ketoamides according to the proposed mechanism of cycle I, which involves two independent CO-insertion steps.

Diversification of α-ketoamides: Via transamidation reactions with alkyl and benzyl amines at room temperature

A wide range of N-tosyl α-ketoamides underwent transamidation with various alkyl amines in the absence of a catalyst, base, or additive. On the other hand, transamidation in N-Boc α-ketoamides was achieved in the presence of Cs2CO3. The reactions proceede

K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water

While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.

Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides

A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.

Dimethyl Sulfoxide as an Oxygen Atom Source Enabled Tandem Conversion of 2-Alkynyl Carbonyls to 1,2-Dicarbonyls

A tandem transformation of 2-alkynyl carbonyl compounds by means of a CuBr2/I2/DMSO/water system is developed, enabling the fromation of various functionalized 1,2-dicarbonyl compounds, including 1,2-diketones, α-keto amides and α-keto ester. This Cu-promoted iodine-mediated tandem procedure employs DMSO as the oxygen atom source of the formed carbonyl group through iodonium ion formation, nucleophilic DMSO addition and C?C bond cleavage cascades. (Figure presented.).

Palladium-Catalyzed Oxidative C≡C Triple Bond Cleavage of 2-Alkynyl Carbonyl Compounds Toward 1,2-Dicarbonyl Compounds?

A new, general palladium-catalyzed oxidative strategy for the cleavage of the C≡C triple bond is presented. By employing PdCl2, CuBr2, TEMPO and air as the catalytic system and H2O as the carbonyl oxygen atom source, a wide range of 2-alkynyl carbonyl compounds, including 1,3-disubstituted prop-2-yn-1-ones, propiolamides and propiolates, lost an alkynyl carbon to access various 1,2-dicarbonyl compounds, e.g., 1,2-diones, 2-keto amides and 2-keto esters, through Wacker oxidation, intramolecular cyclization and C—C bond cleavage cascades.

Copper-Catalyzed Oxidative Synthesis of α-Ketoamides from Aryl Methyl Ketones and N -Bromobutanimide Using N, N -Dimethylformamide as Dimethylamine Source

A novel and practical Cu(OAc) 2 -catalyzed oxidative synthesis of α-ketoamides from aryl methyl ketones and N -bromobutanimide (NBS) using N, N -dimethylformamide (DMF) as dimethylamine (HNMe 2) source and solvent has been developed under mild conditions. DMF was used as a HNMe 2 source and can be easily converted into HNMe 2 by acid hydrolysis. The mechanistic studies indicate that Cu(OAc) 2 plays a dual role in providing both catalyst and oxidant.

Double carbonylation of iodoarenes in the presence of a pyridinium SILP-Pd catalyst

The efficiency of a palladium catalyst, immobilised on a supported ionic liquid phase (SILP) with adsorbed 1-butyl-4-methylpyridinium chloride, was investigated in aminocarbonylation reactions. Double carbonylation was found to be the main reaction using different iodoarenes and aliphatic amines as substrates. Application of aniline derivatives as nucleophiles led to the exclusive formation of substituted benzamides. The stabilisation effect of the adsorbed pyridinium ionic liquid was compared to that of imidazolium and phosphonium derivatives. It was proved that the pyridinium SILP-palladium catalyst could be reused in at least 10 cycles. Recyclability was tested in five successive runs for all of the substrates.