80326-96-1Relevant academic research and scientific papers
Bifunctional Br?nsted Base Catalyzed Mannich Reaction of β-Alkoxy α-Keto Amides: Stereocontrolled Entry to Functionalized Amino Diols
Echave, Haizea,Bastida, I?aki,López, Rosa,Palomo, Claudio
, p. 11554 - 11558 (2018)
The potential of β-alkoxy α-keto amides as pronucleophiles in the enantioselective Mannich type reaction with p-nosyl imines is presented. The proper combination of β-alkoxy α-keto amides and a squaramide-based Br?nsted base catalyst produced highly enantioenriched Mannich adducts, which may be transformed into functionalized amino diols.
Synthesis of 2,3-allenylamides utilizing [1,2]-phospha-Brook rearrangement and their application to gold-catalyzed cycloisomerization providing 2-aminofuran derivatives
Kondoh, Azusa,Ishikawa, Sho,Aoki, Takuma,Terada, Masahiro
supporting information, p. 12513 - 12516 (2016/10/24)
An efficient synthetic method for 2,3-allenylamides having an oxygen functionality at the 2-position, which are difficult to access by conventional methods, was newly developed by utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis. Further manipulation of the 2,3-allenylamides via gold-catalyzed cycloisomerization enables the formation of 2-aminofuran derivatives.
Room-Temperature Decarboxylative Couplings of α-Oxocarboxylates with Aryl Halides by Merging Photoredox with Palladium Catalysis
Cheng, Wan-Min,Shang, Rui,Yu, Hai-Zhu,Fu, Yao
supporting information, p. 13191 - 13195 (2015/09/15)
Enabled by merging iridium photoredox catalysis and palladium catalysis, α-oxocarboxylate salts can be decarboxylatively coupled with aryl halides to generate aromatic ketones and amides at room temperature. DFT calculations suggest that this reaction proceeds through a Pd0-PdII-PdIII pathway, in which the PdIII intermediate is responsible for reoxidizing IrII to complete the IrIII-IrIII-IrII photoredox cycle. Like a mergin': Enabled by merging iridium photoredox catalysis and palladium catalysis, palladium-catalyzed decarboxylative coupling of α-oxocarboxylates with aryl halides can proceed at room temperature. DFT calculations suggest that a Pd0-PdII-PdIII catalytic cycle is merged with an IrIII-IrIII-IrII photoredox cycle, in which PdIII is responsible for oxidizing IrII to complete the photoredox cycle.
Pd/C-catalyzed synthesis of oxamates by oxidative cross double carbonylation of amines and alcohols under Co-catalyst, base, dehydrating agent, and ligand-free conditions
Gadge, Sandip T.,Bhanage, Bhalchandra M.
, p. 6793 - 6797 (2013/07/26)
This work reports a mild, efficient, and ligand-free Pd/C-catalyzed protocol for the oxidative cross double carbonylation of amines and alcohols. Notably, the reaction does not requires any base, co-catalyst, dehydrating agent, or ligand. Pd/C solves the problem of catalyst recovery, and the catalyst was recycled up to six times.
Practical synthesis of functionalized 1,5-disubstituted 1,2,4-triazole derivatives
Xu, Yingju,McLaughlin, Mark,Bolton, Emily N.,Reamer, Robert A.
supporting information; experimental part, p. 8666 - 8669 (2011/02/28)
A general approach for the synthesis of 1,5-disubstituted-1,2,4-triazole compounds is described. A series of new oxamide-derived amidine reagents can be accessed in excellent yield with minimal purification necessary. Typically, these amidine reagents are stable crystalline solids and in certain cases were found to exist in a cyclic form as determined by NMR spectroscopy. Under optimized conditions, the direct reaction of these prepared reagents with various hydrazine hydrochloride salts efficiently generates the target triazoles. Both aromatic and aliphatic hydrazines react readily with the amidine reagents under very mild reaction conditions, delivering desired 1,5-disubstituted-1,2,4-triazole derivatives in good yields.
Synthesis and first X-ray structures of cobalt(II) and cobalt(III) complexes bearing 2,4-dioxo-alkanoic acid dialkylamide ligands
Wang, Jian,Morra, Nicholas A.,Zhao, Hongda,Gorman, Jeffrey S.T.,Lynch, Vincent,McDonald, Robert,Reichwein, John F.,Pagenkopf, Brian L.
experimental part, p. 328 - 334 (2009/10/24)
The aerobic oxidation of 5-hydroxy pentenes to trans-tetrahydrofurans (THFs), the Mukaiyama oxidation, has in recent years emerged as a powerful tool in synthetic chemistry. In this report we describe the first crystal structures of 2,4-dioxo-alkanoic acid dialkylamide complexes for both Co(II) and Co(III) salts. The Co(II) structures show an unprecedented arrangement of atoms, with a central Co(II)(H2O)6 flanked by two Co(II) atoms each coordinated with three anionic chelating ligands. The dimeric Co(III) structures show two anionic chelating ligands and bridging hydroxyl groups.
