58804-62-9

Upstream product

• 39716-58-0 pent-4-enoyl chloride 
• 62-53-3 aniline 
• 42332-07-0 5-ethoxy-pent-1-en-4-yne 
• 74-85-1 ethene 
• 103-71-9 phenyl isocyanate 
• 106-95-6 allyl bromide 
• 103-84-4 Acetanilid 
• 591-80-0 pent-4-enoic acid 
• 59239-04-2 (E)-1-phenylpent-4-en-1-one oxime 
• 1483-35-8 pent-2-enanilide 
• 13555-65-2 pent-2-enoic acid anilide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 59239-04-2 1-phenyl-4-penten-1-one oxime 
• 1436427-79-0 N-methoxypent-4-enamide 

Downstream Products

• 81912-11-0 5-hydroxy-4-methyl-N, 5-diphenyl-2-pentenamide 
• 108078-64-4 5-[(phenylsulfanyl)methyl]dihydrofuran-2(3H)-2-one 
• 6724-71-6 5-methyl-1-phenylpyrrolidin-2-one 
• 18133-14-7 2-(hydroxymethyl)-N-phenylpyrrolidine 
• 119475-54-6 2-(N-acetyl-N-phenylamino)-5methyl-3-phenylcarbamoylthiophene 
• 1208517-76-3 (E)-5-oxo-5-(phenylamino)pent-2-enyl acetate 
• 1367872-46-5 N-[(2Z)-5-{[(4-nitrophenyl)sulfanyl]methyl}dihydrofuran-2(3H)-ylidene]phenylaminium perchlorate 
• 1367872-43-2 N-[(2Z)-5-{[(4-methylphenyl)sulfanyl]methyl}dihydrofuran-2(3H)-ylidene]phenylaminium perchlorate 
• 108078-65-5 5-[(4-tolylsulfanyl)methyl]dihydrofuran-2(3H)-2-one 
• 1367872-59-0 5-{[(4-nitrophenyl)sulfanyl]methyl}dihydrofuran-2(3H)-2-one 
• 1367872-63-6 N-[5-{[(4-nitrophenyl)sulfanyl]methyl}dihydrofuran-2(3H)-ylidene]-N-phenylamine 
• 1367872-40-9 N-{(2Z)-5-[(phenylsulfanyl)methyl]dihydrofuran-2(3H)-ylidene}phenylaminium perchlorate 
• 1427729-21-2 2-(non-2-yn-1-yl)-1-phenylpyrrolidine 
• 1266062-90-1 2-(4-fluorobenzyl)-1-phenylpyrrolidine 

Relevant academic research and scientific papers

The structural requirements of histone deacetylase inhibitors: SAHA analogs modified at the C5 position display dual HDAC6/8 selectivity

Histone deacetylase (HDAC) proteins have emerged as important targets for anti-cancer drugs, with four small molecules approved for use in the clinic. Suberoylanilide hydroxamic acid (Vorinostat, SAHA) was the first FDA-approved HDAC inhibitor for cancer

Extended Hydrogen Bond Networks for Effective Proton-Coupled Electron Transfer (PCET) Reactions: The Unexpected Role of Thiophenol and Its Acidic Channel in Photocatalytic Hydroamidations

Preorganization and aggregation in photoredox catalysis can significantly affect reactivities or selectivities but are often neglected in synthetic and mechanistic studies, since the averaging effect of flexible ensembles can effectively hide the key activation signatures. In addition, aggregation effects are often overlooked due to highly diluted samples used in many UV studies. One prominent example is Knowles's acceleration effect of thiophenol in proton-coupled electron transfer mediated hydroamidations, for which mainly radical properties were discussed. Here, cooperative reactivity enhancements of thiophenol/disulfide mixtures reveal the importance of H-bond networks. For the first time an in-depth NMR spectroscopic aggregation and H-bond analysis of donor and acceptor combined with MD simulations was performed revealing that thiophenol acts also as an acid. The formed phosphate-H+-phosphate dimers provide an extended H-bond network with amides allowing a productive regeneration of the photocatalyst to become effective. The radical and acidic properties of PhSH were substituted by Ph2S2 and phosphoric acid. This provides a handle for optimization of radical and ionic channels and yields accelerations up to 1 order of magnitude under synthetic conditions. Reaction profiles with different light intensities unveil photogenerated amidyl radical reservoirs lasting over minutes, substantiating the positive effect of the H-bond network prior to radical cyclization. We expect the presented concepts of effective activation via H-bond networks and the reactivity improvement via the separation of ionic and radical channels to be generally applicable in photoredox catalysis. In addition, this study shows that control of aggregates and ensembles will be a key to future photocatalysis.

Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization-Hydroboration of Unactivated Alkenes

A tungsten-catalyzed hydroboration of unactivated alkenes at distal C(sp3)-H bonds aided by native directing groups is described herein. The method is characterized by its simplicity, exquisite regio- and chemoselectivity, and wide substrate scope, offering a complementary site-selectivity pattern to other metal-catalyzed borylation reactions and chain-walking protocols.

Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification

Genome mining of microbial natural products enables chemists not only to discover the bioactive molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate-forming enzyme that adenylates a unique building block, 3-isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile natural product SF2768 produced by Streptomyces thioluteus, and this AMP-ligase was demonstrated to accept a broad range of short-chain fatty acids (SCFAs). Herein, we repurpose SfaB to catalyze amidation or thioesterification between those SCFAs and various amine or thiol nucleophiles, thereby providing an alternative enzymatic approach to prepare the corresponding amides and thioesters in vitro.

Practical Synthesis of Halogenated N-Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.

Photoredox-Catalyzed Difunctionalization of Unactivated Olefins for Synthesizing Lactam-Substituted gem-Difluoroalkenes

Herein, the synthesis of lactam-substituted gem-difluoroalkenes has been developed through a photoredox-catalyzed radical cascade reaction. This developed photoredox-catalyzed, Br?nsted base-assisted intramolecular 5-exo-trig cyclization/intermolecular radical addition/β-fluoride elimination reaction offers a simple method for producing lactam, carbamate, or urea-substituted gem-difluoroalkenes with good functional group tolerance and high yields.

Nickel-Catalyzed anti-Markovnikov Hydrodifluoroalkylation of Unactivated Alkenes

An efficient Ni-catalyzed hydrodifluoroalkylation of unactivated alkenes with bromodifluoroacetate by using PhSiH3 as hydride source was developed. The transformation affords aliphatic difluorides with anti-Markovnikov regioselectivity. A wide range of hi

Visible-light-induced Beckmann rearrangement by organic photoredox catalysis

A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.

An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism

Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.

Anti-Markovnikov Hydroazidation of Alkenes by Visible-Light Photoredox Catalysis

The anti-Markovnikov hydroazidation of alkenes has been accomplished under visible-light irradiation by using [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as the photocatalyst and trimethylsilyl azide as the azidating agent. The reactions were greatly facilitated by water, the beneficial effect of which can be attributed to its participation in the reaction as the hydrogen donor, as indicated by deuterium isotope experiments. The reactions proceed under solvent free conditions in the presence of water. 4-Dimethylaminopyridine also exhibited a beneficial effect on the reactions. The present method enabled hydroazidation of several types of unactivated alkenes with good yields and high regioselectivity.