1449418-01-2

Upstream product

• 2564-83-2 2,2,6,6-tetramethyl-piperidine-N-oxyl 
• 100-42-5 styrene 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 211562-21-9 sodium 2,2,6,6-tetramethylpiperidine-1-oxide 

Downstream Products

• 1404079-31-7 2-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)ethanamine 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 1210937-93-1 1-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethan-1-ol 
• 1449418-23-8 1-(2-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)ethyl)-1H-benzo[d][1,2,3]triazole 
• 1449418-24-9 2,2,6,6-tetramethyl-1-(1-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethoxy)piperidine 
• 1449418-28-3 1-(2-(4-(2,5,8,11,14-pentaoxapentadecyl)-1H-1,2,3-triazol-1-yl)-1-phenylethoxy)-2,2,6,6-tetramethylpiperidine 
• 124718-87-2 2-azido-1-phenylethan-1-ol 

Relevant academic research and scientific papers

Oxoammonium Salt-Mediated Vicinal Oxyazidation of Alkenes with NaN3: Access to β-Aminooxy Azides

An approach to the vicinal oxyazidation of alkenes has been achieved under mild and transition metal-free conditions. This method utilizes NaN3 as the azidation agent and 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO

ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS

The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.

Visible-light activated metal catalyst-free vicinal diazidation of olefins with sulfonium iodate(i) species

A visible light-induced vicinal diazidation of various alkenes using stable sulfonium bis(acetoxy)iodate(i) and sodium azide as a radical precursor is described. The trimethylsulfonium [bis(azido)iodate(i)] species, intrinsically generated in situ, demonstrated unprecedented reactivity toward CC π bond-promoting selective azidation under photochemical conditions without any photoredox or metal catalyst. The visible-light stimulated diazidation reaction provides a convenient and straightforward approach to highly prevalent vicinal nitrogen scaffolds of myriad therapeutic importance.

Photoswitchable Regiodivergent Azidation of Olefins with Sulfonium Iodate(I) Reagent

Photoswitchable strategy for selective azidation of structurally diverse olefins under transition-metal-free conditions is reported. The unprecedented reactivity of trimethylsulfonium [bis(azido)iodate(I)] species under visible light allows radical azidooxygenation of the C═C πbond with distinctive selectivity. In the absence of visible light, the reaction proceeds through an ionic intermediate which led to complementary regioselectivity to provide α-alkyl azides. Mechanistic studies reveal that light-controlled regiodivergent azidation involving radical or an ionic pathway can be accomplished with exclusive regioselectivity.

Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins

We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.

Visible-Light-Accelerated Copper(II)-Catalyzed Regio- and Chemoselective Oxo-Azidation of Vinyl Arenes

The visible-light-accelerated oxo-azidation of vinyl arenes with trimethylsilylazide and molecular oxygen as stoichiometric oxidant was achieved. In contrast to photocatalysts based on iridium, ruthenium, or organic dyes, [Cu(dap)2]Cl or [Cu(dap)Cl2] were found to be unique for this transformation, which is attributed to their ability to interact with the substrates through ligand exchange and rebound mechanisms. CuII is proposed as the catalytically active species, which upon coordinating azide will undergo light-accelerated homolysis to form CuI and azide radicals. This activation principle (CuII-X→CuI+X.) opens up new avenues for copper-based photocatalysis.

Iodoazidation of Alkenes by Using Iodine Pentafluoride-Pyridine-Hydrogen Fluoride and Trimethylsilyl Azide

Iodoazidation of alkenes was carried out by using iodine pentafluoride-pyridine-hydrogen fluoride and trimethylsilyl azide. In the reactions of terminal alkenes, anti-Markovnikov products were formed selectively. Cyclohexene gave a mixture of cis- and trans-adducts. These results suggest the involvement of radical species in the reaction.

Stereoselective radical azidooxygenation of alkenes

Radical azidooxygenation of various alkenes is described. A readily prepared N3-iodine(III) reagent acts as a clean N3-radical precursor. Radical generation is achieved with TEMPONa acting as a mild organic reducing reagent. The C-radical generated after N3-radical addition is efficiently trapped by in situ generated TEMPO. Yields are good to excellent, and for cyclic systems azidooxygenation occurs with excellent diastereoselectivity.