906451-51-2

Upstream product

• 136144-39-3 cis-6-iodo-2-hexene 
• 70-55-3 toluene-4-sulfonamide 
• 1143-01-7 N-hexyl p-toluenesulfonamide 
• 928-91-6 (Z)-4-hexenol 
• 60653-76-1 Methanesulfonic acid (Z)-hex-4-enyl ester 
• 110-87-2 3,4-dihydro-2H-pyran 
• 99097-67-3 (Z)-2-(hex-4-en-1-yl)isoindoline-1,3-dione 
• 928-92-7 (E)-hex-4-en-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 120788-32-1 (Z)-4-hexenylamine 

Downstream Products

• 116699-99-1 1-tosyl-2-vinyl-pyrrolidine 
• 1265228-84-9 C₁₃H₁₅⁽²⁾H₂NO₂S 
• 1265228-80-5 C₁₃H₁₄⁽²⁾H₃NO₂S 
• 54356-23-9 (S)-2-ethyl-1-tosylpyrrolidine 

Relevant academic research and scientific papers

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

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.

Mechanistic studies of wacker-type intramolecular aerobic oxidative amination of alkenes catalyzed by Pd(OAc)2/pyridine

Wacker-type oxidative cyclization reactions have been the subject of extensive research for several decades, but few systematic mechanistic studies of these reactions have been reported. The present study features experimental and DFT computational studies of Pd(OAc)2/pyridine-catalyzed intramolecular aerobic oxidative amination of alkenes. The data support a stepwise catalytic mechanism that consists of (1) steady-state formation of a PdII-amidate-alkene chelate with release of 1 equiv of pyridine and AcOH from the catalyst center, (2) alkene insertion into a Pd-N bond, (3) reversible β-hydride elimination, (4) irreversible reductive elimination of AcOH, and (5) aerobic oxidation of palladium(0) to regenerate the active trans-Pd(OAc)2(py)2 catalyst. Evidence is obtained for two energetically viable pathways for the key C-N bond-forming step, featuring a pyridine-ligated and a pyridine-dissociated PdII species. Analysis of natural charges and bond lengths of the alkene-insertion transition state suggest that this reaction is best described as an intramolecular nucleophilic attack of the amidate ligand on the coordinated alkene.

Electrophilic cyclization of N-alkenylamides using?a chloramine-T/I2 system

A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three- to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the chloramine-T/I2 system functions as an effective iodonium species.

A new, simple synthesis of N-tosyl pyrrolidines and piperidines

Iodocyclization of unsaturated tosylamides promoted by Oxone oxidation of KI afforded, in good yields, N-tosyl iodopyrrolidines and piperidines. A new, simple method for the conversion of alcohols to tosylamides is presented. Georg Thieme Verlag Stuttgart.