61174-97-8Relevant academic research and scientific papers
Study of homo- and cross-coupling competition in the reaction of triarylbismuth(V) dicarboxylates with methyl acrylate in the presence of a palladium catalyst
Moiseev, Dmitry V.,Malysheva, Yulia B.,Shavyrin, Andrey S.,Kurskii, Yury A.,Gushchin, Aleksey V.
, p. 3652 - 3663 (2007/10/03)
Triarylbismuth(V) derivatives Ar3Bi(O2CR)2 (Ar = Ph, m-Tol, p-Tol; R = H, Me, Et, n-Bu, t-Bu, n-C5H 11, CF3, CH2Cl, CCl3, Ph) were prepared in good to excellent yields by reaction of Ar3Bi with equimolar amounts of t-BuOOH in the presence of an acid. These compounds were tested in the C-arylation reaction of methyl acrylate, as a model substrate, in the presence of palladium catalyst (4 mol%). It was found that triphenylbismuth dicarboxylates are very active phenylating agents under mild conditions (20 °C). The effect of the carboxylic group, the effect of the nature of the palladium catalyst and the effect of oxygen on the reactivity of the organobismuth compounds and on the selectivity of the C-arylation reaction were studied. Methyl cinnamate, the C-phenylation product, and biphenyl, the homo-coupling by-product, were obtained in all cases. Triphenylbismuth divalerate Ph3Bi(O2CBu)2 is the most reactive compound among the triphenylbismuth dicarboxylates studied.
Unexpected Formation of Triarylbismuth Diformates in the Oxidation of Triarylbismuthines with Ozone at Low Temperatures
Suzuki, Hitomi,Ikegami, Tohru,Matano, Yoshihiro,Azuma, Nagao
, p. 2411 - 2416 (2007/10/02)
Oxidation of triphenylbismuthine 1 with ozone in toluene at -78 deg C gave, unexpectedly, a high yield of triphenylbismuth diformate 3, which was also obtainable as a minor product by a similar oxidation in ethyl acetate and acetone.An X-ray crystallographic study revealed that compound 3 has C2 symmetry, the geometry around the bismuth atom being best described as a distorted trigonal bipyramid as a result of strong intramolecular interaction between the bismuth and carbonyl oxygen atoms.Treatment of compound 3 with aqueous sodium acetate or halides readily converted it into the corresponding triphenylbismuth diacetate 5 or dihalides 7 - 9.
