120-44-5Relevant articles and documents
Silica-supported orthophosphoric acid (OPA/SiO2): preparation, characterization, and evaluation as green reusable catalyst for pinacolic rearrangement
Billamboz, Muriel,Banaszak, Estelle
, p. 1029 - 1040 (2019)
In this paper, we report an easy-to-prepare, cost-effective, efficient, and reusable silica-supported orthophosphoric acid (OPA) catalyst for pinacolic rearrangement. The surface properties of this catalyst were successfully characterized with the help of 31P NMR, TGA, DSC, FT-IR, titration, and microscopy. OPA, hydrogen bonded on the surface, is actually the active species and the reaction seems to occur in the liquid phase embedded in the silica support. As a consequence, the extracting solvent should be chosen with cautious to guarantee the recyclability of the catalyst. As example, pinacol rearrangement reactions were successfully realized with this catalyst and OPA/SiO2 proved to be as efficient as homogeneous orthophosphoric acid to promote the reaction of pinacol derivatives. When using dichloromethane as extracting solvent, OPA/SiO2 can be reuse up to ten times without a significant loss of activity. After ten runs, no physical damage of the catalyst has been observed by microscopy proving its suitability for such application.
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Ho,Wong
, p. 161 (1975)
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Tadros,W. et al.
, p. 2808 - 2812 (1972)
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Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene
Djukanovic, Dimitrije,Filipponi, Paolo,Heinz, Benjamin,Knochel, Paul,Mandrelli, Francesca,Martin, Benjamin,Mostarda, Serena
supporting information, p. 13977 - 13981 (2021/09/13)
The continuous flow reaction of various aryl or heteroaryl bromides in toluene in the presence of THF (1.0 equiv) with sec-BuLi (1.1 equiv) provided at 25 °C within 40 sec the corresponding aryllithiums which were acylated with various functionalized N,N-
Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids
Betori, Rick C.,Davies, Anna V.,Fitzpatrick, Keegan P.,Scheidt, Karl A.
supporting information, p. 9143 - 9148 (2020/03/30)
As a key element in the construction of complex organic scaffolds, the formation of C?C bonds remains a challenge in the field of synthetic organic chemistry. Recent advancements in single-electron chemistry have enabled new methods for the formation of various C?C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical–radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.