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JOURNAL OF ORGANIC CHEMISTRY · 2020 · IF 4.335

Copper-Catalyzed Three-Component Redox-Neutral Ring Opening of Benzothiazoles to 1-Amino-N-(2-(phenylthio)phenyl)methanimine

Nian Zheng,Ce Liu,Ya-Nan Ding,Wei-Yu Shi,Bo-Sheng Zhang,Yong-Min Liang

Copper-catalyzed three-component redox-neutral ring opening of benzothiazoles with aryl iodides and O-benzoyl hydroxylamines for the synthesis of 1-amino-N-(2-(phenylthio)phenyl)methanimine has been developed. This one-pot reaction undergoes C–S and N–O bond cleavage and new C–S and C–N bond construction. Several control experiments excluded a free radical procedure and also demonstrated the secondary amine as a possible intermediate, which was vital to the catalytic reaction. Meanwhile, the deuteration experiment got rid of the C–H activation dehydroisomerization of the benzothiazole mechanism.

研究领域: 有机化学 · 合成化学

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ACS Applied Polymer Materials · 2025 · IF 4.7

Monomolecular Photoinitiators for Hybrid Light-Curing Systems under UV-LEDs

Xiangzhuo Han,Yingchao Zhang,Jinkai Wang,Zhanchen Cui,Zuosen Shi

Sulfonate oxime ester photoinitiators (PIs) based on a thioether-substituted 1,8-naphthalenedicarboximide backbone exhibit good absorption at the emission wavelengths of commonly used LED lamps (385, 395, and 405 nm). The presence of weak C–S and N–O bonds in the molecular structure enables them to be cleaved under light, which leads to the generation of free radicals and cations with efficient initiation properties. Electron paramagnetic resonance spectroscopy supports the mechanism of C–S bond cleavage to produce free radicals, and UV–visible real-time spectroscopy in the presence of Rhodamine B base supports the mechanism of N–O bond cleavage to produce acids. These compounds are high-performance photoinitiators without any other additives for the polymerization of double-bonded compounds and epoxides. They can be initiated at low concentrations when exposed to UV-LEDs. These photoinitiators provide important ideas for the design and synthesis of photoinitiators, which have great potential for application in the field of photopolymerization, especially in hybrid light-curing systems.

CAS / MDL: 75-05-8

研究领域: 材料科学 · 光化学 · 聚合物科学

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Copper-Catalyzed Three-Component Redox-Neutral Ring Opening of Benzothiazoles to 1-Amino-N-(2-(phenylthio)phenyl)methanimine

Monomolecular Photoinitiators for Hybrid Light-Curing Systems under UV-LEDs