5436-58-8Relevant articles and documents
[Co(MeTAA)] Metalloradical Catalytic Route to Ketenes via Carbonylation of Carbene Radicals
Chirila, Andrei,van Vliet, Kaj M.,Paul, Nanda D.,de Bruin, Bas
supporting information, p. 2251 - 2258 (2018/04/09)
An efficient synthetic strategy towards beta-lactams, amides, and esters involving “in situ” generation of ketenes and subsequent trapping with nucleophiles is presented. Carbonylation of carbene radical intermediates using the cheap and highly active cobalt(II) tetramethyltetraaza[14]annulene catalyst [Co(MeTAA)] provides a convenient one-pot synthetic protocol towards substituted ketenes. N-tosylhydrazones are used as carbene precursors, thereby bridging the gap between aldehydes and ketenes. Activation of these carbene precursors by the metalloradical cobalt(II) catalyst affords CoIII-carbene radicals, which subsequently react with carbon monoxide to form ketenes. In the presence of a nucleophile (imine, alcohol, or amine) in the reaction medium the ketene is immediately trapped, resulting in the desired products in a one-pot synthetic protocol. The β-lactams formed upon reaction with imines are produced in a highly trans-selective manner.
Oxidation of Alkynes by Hydrogen Peroxide Catalyzed by Methylrhenium Trioxide
Zhu, Zuolin,Espenson, James H.
, p. 7728 - 7732 (2007/10/03)
The oxidation of alkynes with hydrogen peroxide is catalyzed by methylrhenium tioxide.The reactions can be rationalized by postulating that an oxirene intermediate is formed between a rhenium peroxide and the alkyne.Internal alkynes yield α-diketones and carboxylic acids, the latter from the complete cleavage of the triple bonds.Rearrangement products were observed only for aliphatic alkynes.Terminal alkynes gave carboxylic acids and their derivatives and α-keto acids as the major products, but their yields varied with the solvent used.
RHODIUM(I) CATALYZED CARBONYLATION REACTIONS OF HALIDES AND ETHERS
Buchan, Caroline,Hamel, Nathalie,Woell, James B.,Alper, Howard
, p. 5743 - 5746 (2007/10/02)
Benzylic bromides and methyl ioide react with ethers, carbon monoxide, potassium iodide, and the dimer of chloro(1,5-hexadiene)rhodium(I) to give esters in good yields.