Iron(II)‐catalyzed oxidative coupling of vicinal diols and 2‐amino‐1,4‐naphthoquinone for the synthesis of pyrrolonaphthoquinones and furanonaphthoquinones

Author(s):  
Sujit Maity ◽  
Sandip Kumar Gupta ◽  
Niranjan Panda
2020 ◽  
Author(s):  
Alexis Wolfel ◽  
Cecilia Inés Alvarez Igarzabal ◽  
Marcelo Ricardo Romero

<p>Design of materials with novel sensitivities and smart behaviour is important for the development of smart systems with automated responsiveness. We have recently reported the synthesis of hydrogels, cross-linked by <i>N,N'</i>-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating valuable a-oxo-aldehyde functional groups, useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from <a>2-aminoethyl methacrylate </a>hydrochloride (AEMA), coexisting with DAT into the same network. The a-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds. In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a time-window in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.</p>


2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.


2019 ◽  
Vol 9 (6) ◽  
pp. 1349-1356 ◽  
Author(s):  
Johnny Zhu Chen ◽  
Zhenwei Wu ◽  
Xiaoben Zhang ◽  
Slgi Choi ◽  
Yang Xiao ◽  
...  

Identification of a Pt3Bi nanoscale, surface intermetallic alloy catalyst for non-oxidative coupling of methane (NOCM).


2015 ◽  
Vol 44 (4) ◽  
pp. 1612-1626 ◽  
Author(s):  
Pedro Adão ◽  
Sónia Barroso ◽  
M. Fernanda N. N. Carvalho ◽  
Carlos M. Teixeira ◽  
Maxim L. Kuznetsov ◽  
...  

Several chiral amino acid-derived CuII complexes were prepared and used as catalysts in the aerobic oxidative coupling of 2-naphthol. Moderate homocoupling product yields and enantiomeric excesses were obtained under mild, aqueous conditions.


2021 ◽  
Author(s):  
P. Saychu ◽  
M. Thanasiriruk ◽  
C. Khajonvittayakul ◽  
R. Viratikul ◽  
V. Tongnan ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document