Lewis Acid Mediated Reactions of Zirconacyclopentadienes with Aldehydes: One-Pot Synthetic Route to Indene and Cyclopentadiene Derivatives from Aldehydes and Benzyne or Alkynes

Author(s):  
Changjia Zhao ◽  
Pixu Li ◽  
Xiaoyu Cao ◽  
Zhenfeng Xi
Keyword(s):  
Synthesis ◽  
2020 ◽  
Author(s):  
Sure Siva Prasad ◽  
Dirgha Raj Joshi ◽  
Ikyon Kim

AbstractA highly efficient synthetic route to polysubstituted 2H-chromenes was developed utilizing a domino O-alkylation/intramolecular Horner–Wadsworth–Emmons (HWE) olefination of diarylmethylphosphonates, which were readily accessed via Lewis acid mediated one-pot three-component coupling of aldehydes, phenols, and triethyl phosphite.


2017 ◽  
Vol 53 (74) ◽  
pp. 10263-10266 ◽  
Author(s):  
Abhijit Mal ◽  
Gaurav Goswami ◽  
Imtiyaz Ahmad Wani ◽  
Manas K. Ghorai

A novel synthetic route to functionalized indolinesviaLewis acid catalyzed ring-opening of activated aziridines followed by Cu(OAc)2-mediated intramolecular C–H amination in one-pot with excellent enantio- and diastereospecificity (ee 99%; de >99%).


2019 ◽  
Vol 11 (4) ◽  
pp. 490-506 ◽  
Author(s):  
K. Radhakrishnan ◽  
P. Panneerselvam ◽  
M. Marieeswaran

In this work, a green synthetic route was used to create a number of surface passivated fluorescent carbon quantum dots, which are explored as promising sensing probes, via facile one-pot hydrothermal methods.


2004 ◽  
Vol 82 (10) ◽  
pp. 1452-1461 ◽  
Author(s):  
Pascal Mongrain ◽  
Jasmin Douville ◽  
Jonathan Gagnon ◽  
Marc Drouin ◽  
Andreas Decken ◽  
...  

The strong Lewis acid tungsten oxo complex of calix[4]arene can be obtained in both hydrated and non-hydrated forms. This complex coordinates a water molecule inside the cavity via strong O···W interactions with relatively short distances of 2.284(4) and 2.329(2) Å for the tungsten oxo complex of calix[4]arene··H2O·aniline (1), and the tungsten oxo complex of calix[4]arene·H2O·toluene (2·toluene), respectively. The strong interactions are also deduced by the relatively high H2O elimination temperature observed by TGA and DSC (above 200 °C). The coordinated water molecule inside the calix[4]arene cavity is characterized by a strong IR absorption at 3616 cm–1, and a narrow resonance at ~1.2 ppm (the chemical shifts of the uncoordinated water are 1.55 and 1.60 ppm in C6D6 and CDCl3, respectively). This water molecule gives rise to H-bonds with aniline in 1. The tungsten oxo complex of 5,11,17,23-tetrabromocalix[4]arene (4), also binds H2O as the characteristic signatures are observed. The successful removal of H2O in 2, is performed under mild conditions using bis(tetrahydrofuran)-uranyl nitrate as a competitive Lewis acid. When this reaction is performed in acetonitrile, butyronitrile or tert-butylnitrile, the corresponding tungsten oxo complexes of calix[4]arene·acetonitrile (3), ·butyronitrile (5), and ·tert-butylnitrile (6) are obtained. The use of uranyl as a H2O abstractor is unprecedented. The X-ray structure of 3 consists of a tungsten oxo complex of calix[4]arene coordinated by an acetonitrile molecule (d(W···N = 2.412(2) Å). The tetra-5,11,17,23-choromethyl-25,26,27,28-tetrahydroxycalix[4]arene reacts with M(O)Cl4 (M = Mo, W) in a 1:1 stoichiometry, via a tetra Friedel–Crafts addition of benzene or toluene, followed by a lower-rim complexation of the metal oxide, to form "flower-shaped" calix[4]arenes. This "one pot" double functionalization is unprecedented.Key words: calix[4]arene, tungsten, molybdenum, X-ray, host–guest, Friedel–Crafts, Lewis acid, uranyl, DSC, TGA.


Tetrahedron ◽  
2006 ◽  
Vol 62 (17) ◽  
pp. 4059-4064 ◽  
Author(s):  
Rina Ghosh ◽  
Swarupananda Maiti ◽  
Arijit Chakraborty ◽  
Santu Chakraborty ◽  
Alok K. Mukherjee

2014 ◽  
Vol 50 (82) ◽  
pp. 12270-12272 ◽  
Author(s):  
V. P. Alex Raja ◽  
Giammarco Tenti ◽  
Subbu Perumal ◽  
J. Carlos Menéndez

Pyridines and fused pyridines are accessible by a combination of a Lewis acid-catalyzed multicomponent reaction and aromatization involving loss of a 2-furylmethyl chain.


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