1119121-89-9

Upstream product

• 870-63-3 prenyl bromide 
• 317842-46-9 N-(2-hydroxyethyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 14316-14-4 N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide 

Downstream Products

• 1412894-66-6 N-(2-iodoethyl)-4-methyl-N-(3-methylbut-2-enyl)benzenesulfonamide 
• 1256292-35-9 3-isopropyl-1-tosylpyrrolidine 
• 1412894-67-7 3-(prop-1-en-2-yl)-1-tosylpyrrolidine 

Relevant academic research and scientific papers

Synthesis of All-Carbon Quaternary Centers by Palladium-Catalyzed Olefin Dicarbofunctionalization

The redox-neutral dicarbofunctionalization of tri- and tetrasubstituted olefins to form a variety of (hetero)cyclic compounds under photoinduced palladium catalysis is described. This cascade reaction process was used to couple styrenes or acryl amides with a broad range of highly decorated olefins tethered to aryl or alkyl bromides (>50 examples). This procedure enables one or two contiguous all-carbon quaternary centers to be formed in a single step. The products could be readily diversified and applied in the synthesis of a bioactive oxindole analogue.

Thiocyanate radical mediated dehydration of aldoximes with visible light and air

We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.

Palladium-Catalyzed Carbocyclizations of Unactivated Alkyl Bromides with Alkenes Involving Auto-tandem Catalysis

The development of a general catalytic system for the palladium-catalyzed carbocyclization of unactivated alkyl bromides with alkenes is described. This approach uses a commercially available bisphosphine ligand and avoids the use of carbon monoxide atmosphere present in prior studies involving alkyl iodides. Detailed mechanistic studies of the transformation are performed, which are consistent with auto-tandem catalysis involving atom-transfer radical cyclization followed by catalytic dehydrohalogenation. These studies also suggest that reactions involving alkyl iodides may proceed through a metal-initiated, rather than metal-catalyzed, radical chain process.

Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)5 and Phenanthroline System

An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)5] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)5, 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.

Synthesis of Five-, Six-, and Seven-Membered 1,3- and 1,4-Heterocyclic Compounds via Intramolecular Hydroalkoxylation/Hydrothioalkoxylation of Alkenols/Thioalkenols

Intramolecular hydroalkoxylation/hydrothioalkoxylation of nitrogen-tethered alkenes and alcohols/thiols mediated by boron trifluoride etherate leads to five-membered thiazolidine, six-membered 1,4-oxazines (morpholines) and tetrahydro-2H-1,4-thiazines (th

An efficient synthesis of pyrano [4,5-c] pyrrole derivatives through microwave-accelerated intramolecular Knoevenagal hetero Diels-Alder reaction

Synthesis of novel pyranopyrrole derivatives has been achieved by a one-pot IMHDA reaction of N-substituted aldehydes with various diones in the presence of ethylene diaminediacetate (EDDA) in excellent yields under mild conditions.

A novel heterotricyclic assembly through intramolecular imino Diels-Alder reaction: synthesis of pyrrolo[3,4-b]quinolines

The synthesis of a series of hexahydropyrrolo[3,4-b]quinolines has been achieved in excellent yields by the reaction of aldimines derived from aromatic amines and N-prenylated aliphatic aldehydes in acetonitrile with InCl3 as a catalyst in a sh