139016-16-3Relevant academic research and scientific papers
Reactivity of naphthol towards nucleophiles in anodic oxidation
El-Seedi, Hesham R,Yamamura, Shosuke,Nishiyama, Shigeru
, p. 7485 - 7489 (2002)
Reactivity of the anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles has been investigated. The reaction with electron-rich alkenic nucleophiles such as 1-methoxy-4-propenylbenzene 2 and isosafrole 3 gave a very high yield, whereas the reaction with dihydropyran 4 and dihydrofuran 5 gave a moderate yield, but with ethyl vinyl ether 6 gave a very low yield of the substituted dihydronaphthofuran derivatives 7-10 and 12, respectively. Unexpectedly, the glycosyl derivative 11 was preferentially produced rather than naphthofuran 10 upon using 5 as a nucleophile. In addition, the dimers 15 and 16 were obtained in moderate yield without addition of nucleophile to 1. The mechanism of the oxidation reactions including the [3+2] and [5+2] cycloaddition were discussed.
Covalent Triazine Framework Nanoparticles via Size-Controllable Confinement Synthesis for Enhanced Visible-Light Photoredox Catalysis
Huang, Wei,Huber, Niklas,Jiang, Shuai,Landfester, Katharina,Zhang, Kai A. I.
supporting information, p. 18368 - 18373 (2020/10/02)
For metal-free, organic conjugated polymer-based photocatalysts, synthesis of defined nanostructures is still highly challenging. Here, we report the formation of covalent triazine framework (CTF) nanoparticles via a size-controllable confined polymerization strategy. The uniform CTF nanoparticles exhibited significantly enhanced activity in the photocatalytic formation of dibenzofurans compared to the irregular bulk material. The optoelectronic properties of the nanometer-sized CTFs could be easily tuned by copolymerizing small amounts of benzothiadiazole into the conjugated molecular network. This optimization of electronic properties led to a further increase in observed photocatalytic efficiency, resulting in total an 18-fold enhancement compared to the bulk material. Full recyclability of the heterogeneous photocatalysts as well as catalytic activity in dehalogenation, hydroxylation and benzoimidazole formation reactions demonstrated the utility of the designed materials.
Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols
Blum, Travis R.,Zhu, Ye,Nordeen, Sarah A.,Yoon, Tehshik P.
supporting information, p. 11056 - 11059 (2015/03/30)
We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible-light-activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis suggests that this strategy may be applicable to a variety of useful oxidative transformations.
Anodic oxidation of 4-methoxy-1-naphthol
El-Seedi, Hesham R.,Yamamura, Shosuke,Nishiyama, Shigeru
, p. 3301 - 3304 (2007/10/03)
Anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles provided the corresponding products 8-12 and the dimers 13 and 17 were also produced. The reaction mechanism of the oxidation reaction including the [3+2] cycloaddition was investigated.
Mechanistic Aspects and Synthetic Applications of the Electrochemical and Iodobenzene Bis(trifluoroacetate) Oxidative 1,3-Cycloadditions of Phenols and Electron-Rich Styrene Derivatives
Gates, Bradley D.,Dalidowicz, Peter,Tebben, Andrew,Wang, Shaopeng,Swenton, John S.
, p. 2135 - 2143 (2007/10/02)
Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative.The yield o
