81675-78-7

Upstream product

• 77089-07-7 (4-(vinyloxy)phenyl)methanol 
• 52191-15-8 4-(2-bromoethyloxy)benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 92988-08-4 trivinylboroxin 
• 108-05-4 vinyl acetate 
• 26815-04-3 4-(2-(piperidin-1-yl)ethoxy)benzaldehyde 

Downstream Products

• 1394071-49-8 C₂₆H₂₄N₂O₇ 
• 77089-07-7 (4-(vinyloxy)phenyl)methanol 
• 105355-27-9 Pioglitazone 
• 123-08-0 4-hydroxy-benzaldehyde 

Relevant academic research and scientific papers

Evaluation of 2-(piperidine-1-yl)-ethyl (PIP) as a protecting group for phenols: Stability to ortho-lithiation conditions and boiling concentrated hydrobromic acid, orthogonality with most common protecting group classes, and deprotection via Cope elimination or by mild Lewis acids

A new protecting group, 2-(piperidine-1-yl)-ethyl (PIP), was evaluated as a protecting group for phenols. The PIP group was stable to ortho-lithiation conditions and refluxing with concentrated hydrobromic acid. Deprotection was accomplished by two routes, oxidation to N-oxides followed by Cope elimination (CE) and subsequent hydrolysis or ozonolysis of the vinyl ether or one-step deprotection by BBr3?Me2S. The PIP group is orthogonal to the O-benzyl, O-acetyl, O-t-butyldiphenylsilyl, O-methyl, O-p-methoxybenzyl, O-allyl, O-tetrahydropyranyl and N-t-butoxy carbonyl groups. The CE step was systematically studied and was found to give higher yields when the reaction was performed in the presence of silylating agents.

Radical Hydroarylation of Functionalized Olefins and Mechanistic Investigation of Photocatalytic Pyridyl Radical Reactions

We report the photoredox alkylation of halopyridines using functionalized alkene and alkyne building blocks. Selective single-electron reduction of the halogenated pyridines provides the corresponding heteroaryl radicals, which undergo anti-Markovnikov addition to the alkene substrates. The system is shown to be mild and tolerant of a variety of alkene and alkyne subtypes. A combination of computational and experimental studies support a mechanism involving proton-coupled electron transfer followed by medium-dependent alkene addition and rapid hydrogen atom transfer mediated by a polarity-reversal catalyst.

A Tetrazine-Labile Vinyl Ether Benzyloxycarbonyl Protecting Group (VeZ): An Orthogonal Tool for Solid-Phase Peptide Chemistry

The vinyl ether benzyloxycarbonyl (VeZ) protecting group is selectively cleaved by treatment with tetrazines via an inverse electron-demand Diels-Alder reaction. This represents a new orthogonal protecting group for solid-phase peptide synthesis, with Fmoc-Lys(VeZ)-OH as a versatile alternative to Fmoc-Lys(Alloc)-OH and Fmoc-Lys(Dde)-OH, as demonstrated by the synthesis of two biologically relevant cyclic peptides.

Visualization of mercury(ii) accumulation: In vivo using bioluminescence imaging with a highly selective probe

Mercury is a highly toxic environmental pollutant that negatively affects human health. Thus, an in vivo method for noninvasive imaging of mercury(ii) and visualization of its accumulation within living systems would be advantageous. Herein, we describe a reaction-based bioluminescent probe for detection of mercury(ii) in vitro and accumulation in vivo. The application of this probe would help to shed light on the intricate contributions of mercury(ii) to various physiological and pathological processes.

'Naked-eye' quinoline-based 'reactive' sensor for recognition of Hg2+ ion in aqueous solution

A new 'naked-eye' quinoline-based 'reactive' ratiometric fluorescent probe was prepared. The reactive stoichiometry of the probe with Hg2+ ion was 2:1. The probe exhibited high selectivity towards Hg2+ ion to other metal ions with a

Mild, selective oxidation of aromatic alcohols using β-cyclodextrin- functionalized glass microparticles: Characterization, stability, and application

The surface of glass microparticle (GMP) was functionalized with β-cyclodextrin (→ GMP-β-CD) and was characterized by x-ray photoelectron spectroscopy (XPS). GMP-β-CD was used to catalyze oxidation of alcohols into aldehydes and katones with excellent yield (86-92%). The modified surface of GMP-β-CD showed no change or degradation after repeated use as confirmed from XPS analysis after 10 cycles. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright

A sensitive colorimetric and ratiometric fluorescent probe for mercury species in aqueous solution and living cells

A highly sensitive and selective fluorescent probe for inorganic and organic mercury species displays colorimetric and ratiometric response in a buffer solution via mercury promoted cleavage reaction. The probe is demonstrated to detect CH3HgCl

A simple and highly selective biomimetic oxidation of alcohols and epoxides with N-bromosuccinimide in the presence of β-cyclodextrin in water

A simple, mild and highly efficient biomimetic oxidation of various alcohols and epoxides with N-bromosuccinimide (NBS) catalyzed by β-cyclodextrin in water has been developed. A series of alcohols and epoxides were oxidized selectively at room temperature in excellent yields. This method is a direct one-pot synthesis under mild conditions using water as solvent and has many advantages over the existing methodologies.

Mild and Efficient Hydrolysis of Aromatic Thioacetals/Thioketals using o-Iodoxybenzoic acid (IBX) in Presence of β-Cyclodextrin in Water

An efficient and user-friendly procedure has been developed for the hydrolysis of thioacetals/thioketals to the corresponding carbonyl compounds in impressive yields with o-iodoxybenzoic acid (IBX) in presence of β-cyclodextrin (β-CD) in water under neutral conditions at room temperature.