6435-79-6

Upstream product

• 22537-07-1 4-pentenyl-1-amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 96-47-9 2-methyltetrahydrofuran 
• 70-55-3 toluene-4-sulfonamide 
• 625-30-9 2-pentylamine 
• 304460-21-7 rac-4-methyl-N-(pentan-2-yl)benzenesulfonamide 
• 626-95-9 1,4-Pentanediol 
• 75-16-1 methylmagnesium bromide 
• 6435-78-5 N-tosylpyrrolidine 
• 106011-68-1 4-methyl-N-pentylbenzenesulfonamide 
• 544-97-8 dimethyl zinc(II) 
• 81097-24-7 N-tosyl-(4-pentenyl)amine 
• 145782-19-0 N-(4-pentyn-1-yl)-4-methyl-benzenesulfonamide 
• 821-09-0 n-Pent-4-enyl alcohol 

Relevant academic research and scientific papers

Intramolecular Hydroalkoxylation/Reduction and Hydroamination/Reduction of Unactivated Alkynes Using a Silane-Iodine Catalytic System

A transition-metal-free silane-iodine catalytic system comprising I 2 and Et 3 SiH promotes intramolecular hydroalkoxylation/reduction and hydroamination/reduction of unactivated alkynes. This system allows the reaction to proceed at room temperature affording 2,4- and 2,5-disubstituted pyrrolidines as well as a 2,3-disubstituted tetrahydrofuran with high diastereoselectivity..

Exploring Electrochemical C(sp3)-H Oxidation for the Late-Stage Methylation of Complex Molecules

The magic methyl effect, a dramatic boost in the potency of biologically active compounds from the incorporation of a single methyl group, provides a simple yet powerful strategy employed by medicinal chemists in the drug discovery process. Despite significant advances, methodologies that enable the selective C(sp3)-H methylation of structurally complex medicinal agents remain very limited. In this work, we disclose a modular, efficient, and selective strategy for the α-methylation of protected amines (i.e., amides, carbamates, and sulfonamides) by means of electrochemical oxidation. Mechanistic analysis guided our development of an improved electrochemical protocol on the basis of the classic Shono oxidation reaction, which features broad reaction scope, high functional group compatibility, and operational simplicity. Importantly, this reaction system is amenable to the late-stage functionalization of complex targets containing basic nitrogen groups that are prevalent in medicinally active agents. When combined with organozinc-mediated C-C bond formation, our protocol enabled the direct methylation of a myriad of amine derivatives including those that have previously been explored for the magic methyl effect. This synthesis strategy thus circumvents multistep de novo synthesis that is currently necessary to access such compounds and has the potential to accelerate drug discovery efforts.

Aza-heterocycles via copper-catalyzed, remote C–H desaturation of amines

A majority of medicines contain a nitrogen atom within a five- or six-membered ring. To rapidly access both such aza-heterocycles, we sought to develop a remote C–H desaturation of amines. Inspired by the Hofmann-L?ffler-Freytag (HLF) synthesis of five-me

Bis(trifluoromethanesulfonimide) (BSI): Acidity and application to hydrofunctionalization as a Br?nsted acid catalyst

A binaphthyl derivative, bearing bis(trifluoromethanesulfonimide) (BSI) moiety, was developed as a novel Br?nsted acid. Computational prediction of the pKa value of BSI indicated its classification as a strong Br?nsted acid. BSI catalyzed the h

Manganese-Catalyzed N-F Bond Activation for Hydroamination and Carboamination of Alkenes

A visible-light-promoted method for generating amidyl radicals from N-fluorosulfonamides via a manganese-catalyzed N-F bond activation strategy is reported. This protocol employs a simple manganese complex, Mn2(CO)10, as the precatalyst and a cheap silane, (MeO)3SiH, as both the hydrogen-atom donor and the F-atom acceptor, enabling intramolecular/intermolecular hydroaminations of alkenes, two-component carboamination of alkenes, and even three-component carboamination of alkenes. A wide range of valuable aliphatic sulfonamides can be readily prepared using these practical reactions.

Synthesis method for preparing 2-methylpyrrolidine compound through catalytic hydroamination reaction

The invention discloses a synthetic method for preparing a 2-methylpyrrolidine compound by catalyzing a hydroamination reaction, which comprises the following steps: A, sequentially adding a compound1, KI and KHSO4 into a reactor under an open condition;

Redox Neutral Radical-Relay Cobalt Catalysis toward C-H Fluorination and Amination

A redox neutral radical-relay cobalt-catalyzed intramolecular C-H fluorination of N-fluoroamides featuring the in situ formed cobalt fluorides as the latent radical fluorinating agents is reported. Moreover, the reactivity of such a cobalt catalysis could be diverted from C-H fluorination to amination by engineering substrates' conformational flexibility. Preliminary mechanistic studies (UV-vis spectroscopy, cyclic voltammetry studies and DFT calculations, etc.) support the reaction proceeding a redox neutral radical-relay mechanism.

ZnI2/Zn(OTf)2-TsOH: A versatile combined-Acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization

A mild and efficient combined-Acid system using a zinc(ii) salt [ZnI2 or Zn(OTf)2] and p-Toluene sulfonic acid (TsOH) was investigated for catalytic cationic cyclizations, including intramolecular hydrocarboxylation, hydroalkoxylation, hydroamination, hydroamidation, hydroarylation and polyene cyclizations. This reaction provides easy access to five-and six-membered O-and N-containing saturated heterocyclic compounds, tetrahydronaphthalene derivatives and polycyclic skeletons in excellent yield with perfect Markovnikov selectivity and under mild conditions. The operational simplicity, broad applicability, and use of inexpensive commercially available catalysts make this protocol superior to existing methodologies.

Anodic benzylic C(sp3)-H amination: Unified access to pyrrolidines and piperidines

An electrochemical aliphatic C-H amination strategy was developed to access the important heterocyclic motifs of pyrrolidines and piperidines within a uniform reaction protocol. The mechanism of this unprecedented C-H amination strategy involves anodic C-H activation to generate a benzylic cation, which is efficiently trapped by a nitrogen nucleophile. The applicability of the process is demonstrated for 40 examples comprising both 5- and 6-membered ring formations.

Calcium(II)-Catalyzed Intra- and Intermolecular Hydroamidation of Unactivated Alkenes in Hexafluoroisopropanol

A combination of a calcium(II) triflimide salt and hexafluoroisopropanol (HFIP) was found to be a highly efficient promoter system for the intra- and intermolecular hydroamidation of unactivated alkenes. Unlike other methods, a vast array of functional groups is tolerated at the nitrogen and alkene moieties. The reaction produces the corresponding nitrogen-containing compounds in excellent yields and good diastereoselectivities. The use of HFIP as solvent proved crucial for the proper carrying out of this transformation. Its role, as well as that of calcium and its NTf2 ligand, was rationalized by DFT computations. These calculations show how the [(NTf2)Ca(HFIP)n]+ complex can activate the amide via a basic site of the NTf2 ligand and the alkene with one acidic HFIP proton. The acidity of HFIP is exacerbated by the coordination to the calcium center, the more so as n increases.