sonogashira coupling
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2022 ◽  
Author(s):  
Sumitra Karki ◽  
Lucas J. Karas ◽  
Xiqu Wang ◽  
Judy I. Wu ◽  
Ognjen Š. Miljanić

Two diamond-shaped and partially fluorinated dehydrobenz[18]annulene macrocycles have been synthesized through a one-pot synthesis relying on fourfold Sonogashira coupling. Single crystal structures of the prepared macrocycles show continuous columnar stacks of these molecules that are mediated by the fluoroarene–alkyne, arene–alkyne, fluoroarene–fluoroarene, and alkyne–alkyne [π···π] interactions instead of the expected fluoroarene–arene [π···π] interaction.


Synthesis ◽  
2022 ◽  
Author(s):  
Xiang Zhou ◽  
Qianxia Chen ◽  
Zhaoxin Cao ◽  
Fuyi Zhang ◽  
Yufen Zhao

The synthesis of C-3 substituted het(aryl)indole C-nucleoside analogues bearing structurally diverse sugar moieties has been achieved by Sonogashira coupling of terminal sugar alkynes and het(aryl) iodides followed by heteroannulation of the corresponding sugar/het(aryl) alkynes with substituted 2-iodoanilines. This method is simple and general, and is suitable for structurally diverse sugars and various het(aryl) iodides. The terminal sugar alkynes include furanosides, pyranosides, and acyclic sugars with sensitive groups and bulky substituents. The het(aryl) iodides involve iodobenzene, iodothiophene, iodobenzothiophene, and iodobenzofuran. 31 examples have been given and the corresponding 2-het(aryl)indole C-nucleoside analogues are obtained in moderate to excellent yields.


2022 ◽  
Author(s):  
Li Zhang ◽  
Yi Xiao ◽  
Wensheng Mao ◽  
Jiyan Huang ◽  
hongmei huang ◽  
...  

A novel pyrene-pyridyl conjugated oligomer (OPP-OMe) was conveniently prepared by one-pot Sonogashira coupling. Intriguingly, it was found that introducing only one methoxy moiety at the 4-pyridyl position can be sufficient...


2021 ◽  
Vol 23 (1) ◽  
pp. 347
Author(s):  
Mohamed Gamal Mohamed ◽  
Maha Mohamed Samy ◽  
Tharwat Hassan Mansoure ◽  
Chia-Jung Li ◽  
Wen-Cheng Li ◽  
...  

There is currently a pursuit of synthetic approaches for designing porous carbon materials with selective CO2 capture and/or excellent energy storage performance that significantly impacts the environment and the sustainable development of circular economy. In this study we prepared a new bio-based benzoxazine (AP-BZ) in high yield through Mannich condensation of apigenin, a naturally occurring phenol, with 4-bromoaniline and paraformaldehyde. We then prepared a PA-BZ porous organic polymer (POP) through Sonogashira coupling of AP-BZ with 1,3,6,8-tetraethynylpyrene (P-T) in the presence of Pd(PPh3)4. In situ Fourier transform infrared spectroscopy and differential scanning calorimetry revealed details of the thermal polymerization of the oxazine rings in the AP-BZ monomer and in the PA-BZ POP. Next, we prepared a microporous carbon/metal composite (PCMC) in three steps: Sonogashira coupling of AP-BZ with P-T in the presence of a zeolitic imidazolate framework (ZIF-67) as a directing hard template, affording a PA-BZ POP/ZIF-67 composite; etching in acetic acid; and pyrolysis of the resulting PA-BZ POP/metal composite at 500 °C. Powder X-ray diffraction, thermogravimetric analysis, scanning electron microscopy, transmission electron microscopy, and Brunauer–Emmett–Teller (BET) measurements revealed the properties of the as-prepared PCMC. The PCMC material exhibited outstanding thermal stability (Td10 = 660 °C and char yield = 75 wt%), a high BET surface area (1110 m2 g–1), high CO2 adsorption (5.40 mmol g–1 at 273 K), excellent capacitance (735 F g–1), and a capacitance retention of up to 95% after 2000 galvanostatic charge–discharge (GCD) cycles; these characteristics were excellent when compared with those of the corresponding microporous carbon (MPC) prepared through pyrolysis of the PA-BZ POP precursors with a ZIF-67 template at 500 °C.


2021 ◽  
Vol 9 ◽  
Author(s):  
Zhao-Xiang Luo ◽  
Miao Liu ◽  
Tian Li ◽  
De-Cai Xiong ◽  
Xin-Shan Ye

Herein, the convenient one-step electrochemical bromination of glycals using Bu4NBr as the brominating source under metal-catalyst-free and oxidant-free reaction conditions was described. A series of 2-bromoglycals bearing different electron-withdrawing or electron-donating protective groups were successfully synthesized in moderate to excellent yields. The coupling of tri-O-benzyl-2-bromogalactal with phenylacetylene, potassium phenyltrifluoroborate, or a 6-OH acceptor was achieved to afford 2C-branched carbohydrates and disaccharides via Sonogashira coupling, Suzuki coupling, and Ferrier rearrangement reactions with high efficiency. The radical trapping and cyclic voltammetry experiments indicated that bromine radicals may be involved in the reaction process.


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