22744-94-1

Upstream product

• 201230-82-2 carbon monoxide 
• 51246-20-9 1-phenyl-1-iodoethylene 
• 109-89-7 diethylamine 
• 121-44-8 triethylamine 
• 536-74-3 phenylacetylene 
• 83-13-6 diethyl 2-phenylmalonate 
• 2613-89-0 phenylmalonic acid 
• 13939-06-5 molybdenum hexacarbonyl 
• 492-38-6 2-phenylacrylic acid 
• 50-00-0 formaldehyd 
• 4231-26-9 diethylamino-1 phenyl-2 acetylene 
• 591-50-4 iodobenzene 
• 6422-97-5 Sodium; 2-phenyl-acrylate 
• 51491-68-0 2-phenylacrylyl chloride 

Downstream Products

• 22745-00-2 α-Phenyl-β-hydroxylamino-propionsaeure-diethylamid 
• 89333-26-6 N,N-diethyl-2-phenylpropanamide 
• 1507347-39-8 (Z)-N,N-diethyl-4,4,4-trifluoro-2-phenylbut-2-enamide 
• 20897-23-8 N-<2-(Diaethylcarbamoyl)-2-phenyl-aethyl>-α-phenyl-nitron 

Relevant academic research and scientific papers

Copper-catalyzed intermolecular chloro- and bromotrifluoromethylation of alkenes

A highly practical copper-catalyzed intermolecular halotrifluoromethylation of alkenes has been developed under mild reaction conditions. A variety of Cl/Br-containing trifluoromethyl derivatives were directly synthesized from a wide range of alkenes, including electron-deficient and unactivated alkenes.

Palladium-catalyzed regiospecific aminocarbonylation of alkynes in the ionic liquid [bmim][Tf2N]

Regiospecific construction of 2-substituted acrylamides was achieved by palladium-catalyzed aminocarbonylation of alkynes in the ionic liquid [bmim][Tf2N] without any acid additive under relatively mild conditions. The ionic liquid was used as

Improved cyclopropanation activity of histidine-ligated cytochromeP450 enables the enantioselective formal synthesis of levomilnacipran

Engineering enzymes capable of modes of activation unprecedented in nature will increase the range of industrially important molecules that can be synthesized through biocatalysis. However, low activity for a new function is often a limitation in adopting enzymes for preparative-scale synthesis, reaction with demanding substrates, or when a natural substrate is also present. By mutating the proximal ligand and other key active-site residues of the cytochromeP450 enzyme from Bacillus megaterium (P450-BM3), a highly active His-ligated variant of P450-BM3 that can be employed for the enantioselective synthesis of the levomilnacipran core was engineered. This enzyme, BM3-Hstar, catalyzes the cyclopropanation of N,N-diethyl-2-phenylacrylamide with an estimated initial rate of over 1000 turnovers per minute and can be used under aerobic conditions. Cyclopropanation activity is highly dependent on the electronic properties of the P450 proximal ligand, which can be used to tune this non-natural enzyme activity. Old cytochrome, new tricks: Mutation of the proximal Cys residue in the cytochromeP450 enzyme from Bacillus megaterium (P450-BM3) leads to highly active, oxygen tolerant, and enantioselective catalysts for the cyclopropanation of N,N-diethyl-2-phenylacrylamide. Directed evolution of a histidine-ligated P450-BM3 enabled the enantioselective formal synthesis of levomilnacipran.

Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines

Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is proposed for this transformation.

Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent "Ene"-Reductases

Non-natural photoenzymatic reactions reported to date have depended on the excitation of electron donor-acceptor complexes formed between substrates and cofactors within protein active sites to facilitate electron transfer. While this mechanism has unlocked new reactivity, it limits the types of substrates that can be involved in this area of catalysis. Here we demonstrate that direct excitation of flavin hydroquinone within "ene"-reductase active sites enables new substrates to participate in photoenzymatic reactions. We found that by using photoexcitation these enzymes gain the ability to reduce acrylamides through a single electron transfer mechanism.

Erratum: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent 'Ene'-Reductases (J. Am. Chem. Soc. (2021) 143:4 (1735-1739) DOI: 10.1021/jacs.0c11494)

Support by the Department of Energy was inadvertently left out of the Acknowledgments and a coauthor's name was misspelled in the Supporting Information. The scientific part of the manuscript remains unchanged. The complete correct Acknowledgment paragraph is as follows.

Rh-Catalyzed asymmetric hydroaminomethylation of α-Substituted acrylamides: Application in the synthesis of RWAY

The successful rhodium-catalyzed asymmetric hydroformylation and hydroaminomethylation of α-substituted acrylamides is described using 1,3-phosphite-phosphoramidite ligands based on a sugar backbone. A broad scope of chiral aldehydes and amines were afforded in high yields and excellent enantioselectivities (up to 99%). Furthermore, the synthetic potential of this method is demonstrated by the single-step synthesis of the brain imaging molecule RWAY.

Pd-catalyzed hydroaminocarbonylation of alkynes with aliphatic amines and its mechanism study

This work describes the hydroaminocarbonylation of alkynes with aliphatic amines without the addition of any acid additive. Excellent conversion and regioselectivity toward the formation of branched amides were obtained over a dppp-based Pd-catalytic syst

Palladium-Catalyzed Hydroaminocarbonylation of Alkynes with Tertiary Amines via C-N Bond Cleavage

An efficient strategy for the cleavage of the C-N bond of tertiary amines was developed with DTBP as an oxidant, in which the cleaved H atom and amine moiety were successfully transferred to the desired products. This strategy has enabled an efficient palladium-catalyzed hydroaminocarbonylation of alkynes with tertiary amines. Notably, the catalyst loading could be lowered from 5 to 0.1 mol %, which represents the lowest catalyst loading among the reported work on carbonylation via C-N bond activation.

Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization

A palladium-catalyzed C-H bond functionalization of acrylamides was developed to build up stereoselectively trifluoromethylated 1,3-butadienes. Using a tertiary amide as a directing group, olefins were selectively functionalized with 2-bromo-3,3,3-trifluoropropene to access these important fluorinated compounds. The methodology was extended to the construction of pentafluoroethyl-substituted 1,3-dienes. Mechanistic studies supported by density functional theory calculations suggested a redox neutral mechanism for this transformation.