240132-49-4

Upstream product

• 35161-71-8 methyl(propargyl)amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 74-88-4 methyl iodide 
• 106-96-7 propargyl bromide 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 74-83-9 methyl bromide 

Downstream Products

• 927385-34-0 (R)-N-(5-hydroxyhex-2-ynyl)-N-methyl-p-toluenesulfonamide 
• 927385-35-1 (R)-N-methyl-N-(5-(prop-2-ynyloxy)hex-2-ynyl)-p-toluenesulfonamide 
• 1383926-81-5 ((Z)-N-(2-ethoxycyclobutylidene)methyl)-N,4-dimethylbenzenesulfonamide 
• 1383926-91-7 (Z)-N-((2-(N,4-dimethylphenylsulfonamido)-3-methylenecyclobutylidene)methyl)-N,4-dimethylbenzenesulfonamide 
• 1383926-73-5 N,4-dimethyl-N-(propa-1,2-dien-1-yl)benzenesulfonamide 
• 1428369-72-5 C₂₆H₃₁NO₄S 
• 1646624-46-5 (E)-N-((2-benzoyl-2-cyanocyclopropylidene)methyl)-N,4-dimethylbenzenesulfonamide 

Relevant academic research and scientific papers

Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides

Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.

Contractions of 1,4-Diazepines to Pyrroles Triggered by Valence Tautomerization: A One-Pot Approach and Mechanism

Herein, we describe the valence tautomerizations of fused 1,4-diazepines, which are reconstructed to give pyrrole derivatives and HCN gas. Several factors that influence the equilibrium between each valence tautomer of an 8π-electron diazepine skeleton are demonstrated. On the basis of these mechanistic studies, a cascade strategy for the construction of diazepines followed by ring contraction is developed to afford aryl- or alkyl-substituted pyrrolo[1,2-a]quinolines that are otherwise challenging to fabricate. In addition, further transformations of the obtained products highlight the advantages of the developed methodology.

Synergistic Peptide and Gold Catalysis: Enantioselective Addition of Branched Aldehydes to Allenamides

The combination of a peptide catalyst and a gold catalyst is presented for enantioselective addition reactions between branched aldehydes and allenamides. The two catalysts act in concert to provide γ,δ-enamide aldehydes bearing a fully substituted, benzylic stereogenic center – a structural motif common in many natural products and therapeutically active compounds – with good yields and enantioselectivities. The reaction tolerates a variety of alkyl and alkoxy substituted aldehydes and the products can be elaborated into several chiral building blocks bearing either 1,4- or 1,5- functional group relationships. Mechanistic studies showed that the conformational features of the peptide are important for both the catalytic efficiency and stereochemistry, while a balance of acid/base additives is key for ensuring formation of the desired product over undesired side reactions.

Copper-catalysed hydroamination of N-allenylsulfonamides: The key role of ancillary coordinating groups

A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.

Transition-Metal-Free Stereoselective Borylation of Allenamides

Complete stereocontrol on the transition-metal-free hydroboration of the distal double bond of allenamides could be achieved when allenamides contained acetyl substituents, which provided exclusively the Z-isomer. The consecutive Pd-catalyzed cross-coupli

Synthesis, cytotoxicity and anti-cancer activity of new alkynyl-gold(i) complexes

Alkynyl(triphenylphosphine)gold(i) complexes carrying variously substituted propargylic amines have been synthesized and fully characterized in solution and solid state. High levels of toxicity (i.e. micromolar range) were recognized for a series of cance

Gold-Catalyzed Fluorination–Hydration: Synthesis of α-Fluorobenzofuranones from 2-Alkynylphenol Derivatives

The AuI-catalyzed fluorination–hydration of 2-alkynylphenol derivatives in the presence of Selectfluor [1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate)] has been developed. This method provides straightforward a

A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes

Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is

Double transfer of chirality in organocopper-mediated bis(alkylating) cycloisomerization of enediynes

An original synthesis of chiral benzofulvenes triggered by organocopper reagents is reported. These enantiopure products are available through a highly chemo-, regio-, diastereo-, and enantioselective bis(alkylating) cycloisomerization process. A double chirality transfer (central-to-axial-to- central) is observed. Double duty: An original synthesis of chiral benzofulvenes was developed through the highly chemo-, regio-, diastereo-, and enantioselective double transfer of alkyl groups to electrophilic enediynes. This organocopper-triggered cycloisomerization proceeds with double transfer of chirality (central-to-axial-to-central).

Synthesis of 5,6,7,8-tetrahydro-1,6-naphthyridines and related heterocycles by cobalt-catalyzed [2 + 2 + 2] cyclizations

Microwave-promoted, cobalt-catalyzed intramolecular [2 + 2 + 2] cyclizations of dialkynylnitriles successfully gave 5,6,7,8-tetrahydro-1, 6naphthyridines. The efficient synthesis of these relatively simple, yet rarely addressed heterocycles enabled the pr