Published TCIMAIL newest issue No.196
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Organophosphorus catalysts are important compounds used in a variety of synthetic reactions and in drug development. In particular, the redox-neutral phosphine oxide catalyst and multifunctionalized phosphonium salt catalysts have attracted much attention recently. For instance, the phosphine oxide 2-[(diphenyl-phosphoryl)methyl]phenol [H1763] catalyzes the Mitsunobu-type reaction without any by- products from the reagents, except for water. Furthermore, anti-1,2,2,3,4,4-hexamethylphosphetane 1-oxide [H1766] catalyzes deoxygenative C-N cross coupling of nitroarenes with boronic acids to give heteroaryl amines. In addition, MeTAPS salts [H1748] [H1749] can catalyze carbon dioxide fixation reaction under ambient atmosphere to synthesize carbonates from epoxides. The phosphorus ylides synthesized from H1748 or H1749 with the treatment of base can catalyze regioselective acylation of diols.
Advantages
- Easy-to-handle and stable solids
- H1763 catalyzes reagent-derived waste-free Mitsunobu-type reaction.
- H1766 catalyzes the deoxygenative C-N cross-coupling reaction of nitro(hetero)arenes with (hetero)arylboroic acids to form di(hetero)arylamines.
- H1748 and H1749 catalyze carbon dioxide fixation reaction under ambient pressure.
Applications
Waste-free Mitsunobu-type reaction 1)
Deoxygenative C-N cross coupling of nitro(hetero)arenes with (hetero)arylboroic acids 2)
Synthesis of cyclic carbonates through carbon dioxide fixation under ambient pressure 3)
References
- 1) Redox-neutral organocatalytic Mitsunobu reactions
- 2) An Improved PIII/PV=O-Catalyzed Reductive C–N Coupling of Nitroaromatics and Boronic Acids by Mechanistic Differentiation of Rate- and Product-Determining Steps
- 3) A Phosphonium Ylide as an Ionic Nucleophilic Catalyst for Primary Hydroxyl Group Selective Acylation of Diols
