90765-16-5Relevant academic research and scientific papers
Equilibrium shift in the rhodium-catalyzed acyl transfer reactions
Arisawa, Mieko,Igarashi, Yui,Kobayashi, Haruki,Yamada, Toru,Bando, Kentaro,Ichikawa, Takuya,Yamaguchi, Masahiko
, p. 7846 - 7859 (2011/10/12)
Rhodium/phosphine complexes catalyze equilibrium acyl transfer reactions between acid fluorides, aryl esters, acylphosphine sulfides, and thioesters. The use of appropriate co-substrates to accept heteroatom groups shifted the equilibrium to desired products. Acylphosphine sulfides and aryl esters were converted to acid fluorides using benzoylpentafluorobenzene as the fluoride donor, and the fluorination reaction of thioesters employed (4-tolylthio) pentafluorobenzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer reactions proceeded under neutral conditions without using acid or base. The involvement of acyl rhodium intermediates in these reactions was suggested by the carbothiolation reaction of thioesters and alkynes.
A concerted mechanism for the transfer of the thiophosphinoyl group from aryl dimethylphosphinothioate esters to oxyanionic nucleophiles in aqueous solution
Onyido, Ikenna,Swierczek, Krzysztof,Purcell, Jamie,Hengge, Alvan C.
, p. 7703 - 7711 (2007/10/03)
Earlier work on the hydrolysis of aryl phosphinothioate esters has led to contradictory mechanistic conclusions. To resolve this mechanistic ambiguity, we have measured linear free energy relationships (βnuc and βIg) and kinetic isot
