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Synthesis of bis(benzotriazol-1-yl)methane derivatives by cobalt-catalyzed formation of C-C bond

FERRARO, VALENTINA
•
Bortoluzzi, M.
•
Castro, J.
2019
  • conference object

Abstract
The first example of CoCl2-catalyzed reaction between 1,1'-carbonyldiazoles and carbonyl compounds was reported by Thé and Peterson in 1973, obtaining 2,2-di(pirazol-1-yl)propane from di(pyrazol-1-yl)methanone and acetone. The study was extended to several other ketones and aldehydes and to methyl-substituted di(pyrazol-1-yl)methanone derivatives, with the isolation of the corresponding di(pirazol-1-yl)alkanes by elimination of CO2. A reaction mechanism was subsequently proposed. The synthetic approach was then extended to functionalized aldehydes, with the aim of preparing pyrazole-based ligands to be applied in coordination, supramolecular, bioinorganic and organometallic chemistry. To the best of our knowledge, the cobalt-catalyzed reaction was never applied for the synthesis of di(benzotriazol-1-yl)methane derivatives, despite the fact that benzotriazole is considered an ideal synthetic auxiliary in organic chemistry [4]. For instance, di(benzotriazol-1-yl)phenylmethane was obtained following different synthetic approaches with variable selectivity [5]. In this communication we report the straightforward preparation of di(benzotriazol-1-yl)phenylmethane and di(benzotriazol-1-yl)pyridin-2-ylmethane from di(benzotriazol-1-yl)methanone and the proper aldehyde, using CoCl2 as catalyst under neat conditions. The products were characterized spectroscopically and their solid structures were ascertained by single-crystal X-ray diffraction.
Archivio
https://hdl.handle.net/11368/2954450
https://sciforum.net/paper/view/6469
Diritti
open access
license:digital rights management non definito
license uri:iris.pri00
FVG url
https://arts.units.it/bitstream/11368/2954450/10/1_ECSOC2019_Synthesis of di(benzotriazol-1-yl)methane derivatives by cobalt-catalyzed formation of C-C bonds.pdf
Soggetti
  • Benzotriazole

  • Cobalt catalysi

  • C-C formation.

Visualizzazioni
4
Data di acquisizione
Apr 19, 2024
Vedi dettagli
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