Metal-free decarbonylative alkylation–aminoxidation of styrene derivatives with aliphatic aldehydes and N-hydroxyphthalimide

2017 ◽  
Vol 15 (6) ◽  
pp. 1338-1342 ◽  
Author(s):  
Yu-Xia Li ◽  
Qi-Qiang Wang ◽  
Luo Yang

A convenient metal-free decarbonylative alkylation–aminoxidation of styrene derivatives with aliphatic aldehydes and N-hydroxyphthalimide (NHPI) to yield phthalimide protected alkoxyamines was developed for the first time.

2021 ◽  
Author(s):  
Kai Ji ◽  
Ka Lu ◽  
Jie Huang ◽  
Zi-Hao Li ◽  
Tong-Mei Ding ◽  
...  

A highly regio- and diastereo-selective Brønsted acid-catalyzed tandem hydrothiolation/Friedel-Crafts reaction of linear 1,3-dienes has been developed for the first time, which provides a metal-free, atom-economic and concise way of constructing...


2016 ◽  
Vol 12 ◽  
pp. 648-653 ◽  
Author(s):  
Oksana S Mikhalchenko ◽  
Dina V Korchagina ◽  
Konstantin P Volcho ◽  
Nariman F Salakhutdinov

Conditions enabling the single-step preparative synthesis of chiral 4-fluoropolyhydro-2H-chromenes in good yields through a reaction between monoterpenoid alcohols with para-menthane skeleton and aldehydes were developed for the first time. The BF3·Et2O/H2O system is used both as a catalyst and as a fluorine source. The reaction can involve aliphatic aldehydes as well as aromatic aldehydes containing various acceptor and donor substituents. 4-Hydroxyhexahydro-2H-chromenes were demonstrated to be capable of converting to 4-fluorohexahydro-2H-chromenes under the developed conditions, the reaction occurs with inversion of configuration.


2020 ◽  
Vol 56 (44) ◽  
pp. 5901-5904 ◽  
Author(s):  
Erbay Kalay ◽  
Hüseyin Küçükkeçeci ◽  
Haydar Kilic ◽  
Önder Metin

We report for the first time the employment of black phosphorus (BP) as a metal free, visible-light-active and reusable heterogeneous photoredox catalyst for the direct C–H arylation of heteroarenes (furan and thiophene) with aryl diazonium salts.


2015 ◽  
Vol 76 (13) ◽  
Author(s):  
Nor Shuhada Alim ◽  
Hendrik O. Lintang ◽  
Leny Yuliati

In this study, a metal-free carbon nitride (CN) was investigated for the first time as a potential fluorescence sensor for detection of nitrate ions (NO3-). The CN was prepared through thermal polymerization of urea precursor at 823 K and characterized by diffuse reflectance ultraviolet-visible (DR UV-Vis), Fourier transform infrared (FTIR), and fluorescence spectroscopies. The DR UV-Vis spectrum confirmed that CN could absorb light up to 450 nm. On the other hand, the FTIR spectrum revealed the presence of graphitic CN single and double bond characters in the 800-1700 cm-1 region. From the fluorescence spectroscopy, three excitation peaks at 278, 310 and 369 nm were observed due to the presence of N=C, C=O and N-C groups, respectively. The fluorescence sensor capability of the CN was then investigated using concentrations of NO3- in the range of 300-1800 mM. It was confirmed that the intensities of the emission sites were quenched linearly with the concentrations of the NO3-. The CN showed good reproducibility with relative standard deviation (RSD) values were 1.5-7.2%.  These results suggested that CN can act as the fluorescence sensor for NO3-.


Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2395-2409
Author(s):  
Weiwei Qin ◽  
Zhaodong Li ◽  
Yiming Du ◽  
Yue Chen ◽  
Yun-Lin Liu

An efficient, PhI(OAc)2-mediated, radical azidoheteroarylation of alkenes under transition-metal-free conditions is reported by employing TMSN3 and quinoxalin-2(1H)-ones as coupling partners. This domino reaction allows an efficient synthesis of valuable orangoazides containing quinoxalin-2(1H)-one derivatives and could be extended to phosphinyl-alkylated quinoxalin-2(1H)-one in a single step in moderate to excellent yields under mild conditions, as demonstrated by the preliminary antibacterial evaluation against Magnaporthe grisea for the first time. Mechanistic studies revealed that this transformation undergoes a cascade addition pathway controlled by a polar radical.


Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 856-860
Author(s):  
Laurent El Kaïm ◽  
Mansour Dolé Kerim ◽  
Pakoupati Boyode ◽  
Julian Garrec

We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-arylisoxazole derivatives.


2014 ◽  
Vol 50 (85) ◽  
pp. 12880-12883 ◽  
Author(s):  
Kai Sun ◽  
Xin Wang ◽  
Gang Li ◽  
Zhonghong Zhu ◽  
Yongqing Jiang ◽  
...  

A metal-free intermolecular oxidative C–N formation reaction of aryl ethers with saccharins was realized for the first time.


RSC Advances ◽  
2015 ◽  
Vol 5 (70) ◽  
pp. 56865-56871 ◽  
Author(s):  
Hu Liu ◽  
Xingrong Liao ◽  
Xiaoyu Li ◽  
Di Wu ◽  
Qiang Guo ◽  
...  

A novel thieno[1,4]benzothiazine donor has been developed for the first time to construct metal-free organic sensitizers, which exhibit more dramatically red-shifted absorptions than phenothiazine-based dyes.


1979 ◽  
Vol 57 (9) ◽  
pp. 1111-1113 ◽  
Author(s):  
Katherine A. Martin ◽  
Martin J. Stillman

Absorption and magnetic circular dichroism spectra of metal-free phthalocyanine (H2Pc) have been recorded over the range 270–800 nm. The use of solvents transparent in the 270–400 nm region allows the observation for the first time of the B band spectral envelope of H2Pc in solution. The mcd spectrum clearly indicates that the complex (NH4)2Pc is formed when ammonia is bubbled through a solution of H2Pc in dimethyl sulphoxide. The multi-transition nature of the B band region is identified as a property of the phthalocyanine π electron system rather than arising from charge transfer between the ring and a central metal cation.


2017 ◽  
Vol 15 (26) ◽  
pp. 5476-5479 ◽  
Author(s):  
Jin-Tao Yu ◽  
Rongzhen Chen ◽  
Jiawei Zhu ◽  
Jiang Cheng

A metal-free decarbonylative arylalkylation of N-(arylsulfonyl)acrylamides using aliphatic aldehydes as the alkyl radical source was developed.


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