57186-75-1

Upstream product

• 201230-82-2 carbon monoxide 
• 90778-63-5 N-(3-hydroxypent-4-enyl)-4-methylbenzenesulfonamide 
• 694-05-3 1,2,3,6-tetrahydropyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 627-32-7 1-iodopropan-3-ol 
• 347885-68-1 4-bromo-1-tosylpiperidine 
• 557-21-1 zinc(II) cyanide 
• 289890-80-8 4-iodo-1-[(4-methylphenyl)sulfonyl]piperidine 
• 80213-12-3 1-[(4-methylbenzene)-sulfonyl]-4-piperidinol 
• 41979-39-9 4-piperidone hydrochloride 
• 1274845-59-8 1-(1-p-toluenesulfonylpiperidin-4-yl)ethan-1-one 
• 54288-70-9 4-bromopiperidine hydrobromide 
• 606926-42-5 N-(4-methylphenylsulfonyl)-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine 
• 920-39-8 isopropylmagnesium bromide 

Downstream Products

• 1624333-45-4 1-tosyl-4-((trifluoromethyl)thio)piperidine 
• 1251537-47-9 (1-tosylpiperidin-4-yl)boronic acid 

Relevant academic research and scientific papers

Palladium-catalyzed regio- and stereoselective synthesis of N-protected 2,4-dialkylated azacyclobutanes from amino allenes

Palladium-catalyzed reaction of N-arylsulfonyl-1-alkyl-3,4-dienylamines with an aryl iodide in the presence of potassium carbonate in DMF at around 70°C affords most predominantly the 2,4-cis-disubstituted azacyclobutanes bearing an aryl group on the doub

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Activated Hoveyda-Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde

Two EWG-activated Hoveyda-Grubbs-type ruthenium complexes (Sil-II and Sil-II’) were obtained, characterized, and screened in a set of olefin metathesis reactions. These catalysts were conveniently synthesized from a commercially available pharmaceutical building block – Sildenafil aldehyde – in two steps only. Stability and catalytic activity tests disclosed that the bulkier NHC-ligand bearing catalyst Sil-II’ is visibly more stable and productive than its smaller NHC-analogue Sil-II. Good application profile of catalyst Sil-II’ was confirmed in a set of diverse metathesis reactions including ring-closing metathesis (RCM) and cross-metathesis (CM) of complex polyfunctional substrates of medicinal chemistry interest, including a challenging macrocyclization of the Pacritinib precursor. Compatibility of the new catalyst with various green solvents was checked and metathesis of Sildenafil and Tadalafil-based substrates was successfully conducted in acetone. The mechanism of Sil-II’ initiation has been investigated through kinetic experiments unveiling that the decrease of the steric hindrance of the chelating alkoxy moiety (from iPrO to EtO) favors the interchange initiation pathway over the typical dissociation pathway for other popular 2nd generation Hoveyda-Grubbs catalysts. (Figure presented.).

Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins

We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric mixtures, this approach enables, by fine-tuning of the electronic and steric properties of the cobalt catalyst, to obtain high olefin positional selectivity. This unprecedented mechanistic feature has allowed access tocontra-thermodynamic olefins, elusive by E2 eliminations.

Regiocontrolled Reductive Vinylation of Aliphatic 1,3-Dienes with Vinyl Triflates by Nickel Catalysis

The regiocontrolled functionalization of 1,3-dienes has become a powerful tool for divergent synthesis, yet it remains a long-standing challenge for aliphatic substrates. Herein, we report a reductive approach for a branch-selective 1,2-hydrovinylation of aliphatic 1,3-dienes with R-X electrophiles, which represents a new selectivity pattern for diene functionalization. Simple butadiene, aromatic 1,3-dienes, and highly conjugated polyene were also tolerated. The combination of Ni(0) and the phosphine-nitrile ligand generally resulted in >20:1 regioselectivity with the retention of the geometry of the C3-C4 double bonds. This reaction proceeds with a broad substrate scope, and it allows for the conjugation of two biologically active units to form more complex polyene molecules, such as tetraene and pentaene as well as heptaene.

Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2

Cyanation of unactivated primary and secondary alkyl mesylates with Zn(CN)2 catalyzed by nickel has been developed. The reaction provides an efficient route for the synthesis of alkyl nitriles with wide substrate scope, good functional group tolerance, and compatibility with heterocyclic compounds. Mechanistic studies indicate that alkyl iodide generated in situ serves as the reactive intermediate and the gradual release of alkyl iodide is crucial for the success of the reaction.

Triphenylphosphine-Catalyzed Alkylative Iododecarboxylation with Lithium Iodide under Visible Light

Under irradiation of 456 nm blue light-emitting diodes, PPh3 catalyzes the iododecarboxylation of aliphatic carboxylic acid derived N-(acyloxy)phthalimide with lithium iodide as an iodine source. The reaction delivers primary, secondary, and bridgehead te

Design of bis-NHC Ru-complexes featuring diarylmethylene N-substituents for olefin metathesis

New ruthenium indenylidene complexes containing N-heterocyclic carbene (NHC) ligands were synthesized and evaluated in olefin metathesis. The presence of two symmetrical saturated NHCs featuring N-diarylmethylene fragments (R= H, OMe or F) led to robust ruthenium precatalysts with a good latency. A kinetic study was investigated showing that a thermal stimulus (>60 °C) is required to reach an efficient catalytic initiation. Interestingly, a slight electronic effect was observed depending on the presence of an electron-donating or –withdrawing group within the diarylmethylene moiety. These complexes showed good activity at 1 mol% of catalyst loading in selected ring-closing metathesis (RCM) and cross-metathesis (CM) transformations.

Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis

Olefin metathesis is now one of the most efficient ways to create new carbon-carbon bonds. While most efforts focused on the development of ever-more efficient catalysts, a particular attention has recently been devoted to developing latent metathesis cat

Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis

Olefin metathesis is now one of the most efficient ways to create new carbon-carbon bonds. While most efforts focused on the development of ever-more efficient catalysts, a particular attention has recently been devoted to developing latent metathesis cat