26919-48-2Relevant articles and documents
Synthesis of highly functionalized triarylbismuthines by functional group manipulation and use in palladium- and copper-catalyzed arylation reactions
Hébert, Martin,Petiot, Pauline,Benoit, Emeline,Dansereau, Julien,Ahmad, Tabinda,Le Roch, Adrien,Ottenwaelder, Xavier,Gagnon, Alexandre
, p. 5401 - 5416 (2016/07/13)
Organobismuthines are an attractive class of organometallic reagents that can be accessed from inexpensive and nontoxic bismuth salts. Triarylbismuthines are particularly interesting due to their air and moisture stability and high functional group tolerance. We report herein a detailed study on the preparation of highly functionalized triarylbismuth reagents by triple functional group manipulation and their use in palladium- and copper-catalyzed C-, N-, and O-arylation reactions.
Stability and toxicity of tris-tolyl bismuth(v) dicarboxylates and their biological activity towards Leishmania major
Ong, Yih Ching,Blair, Victoria L.,Kedzierski, Lukasz,Tuck, Kellie L.,Andrews, Philip C.
, p. 18215 - 18226 (2015/10/28)
A series of 29 tris-tolyl bismuth(v) di-carboxylato complexes of composition [Bi(Tol)3(O2CR)2] involving either ortho, meta or para substituted tolyl ligands have been synthesized and characterised. Of these 15 were assessed for their toxicity towards Leishmania promastigotes and human fibroblast cells, with ten then being subsequently assessed against parasite amastigotes. The carboxylate ligands are drawn from a series of substituted and biologically relevant benzoic acids which allow a comparison with earlier studies on [BiPh3(O2CR)2] and analogous Sb(v) [SbAr3(O2CR)2] (Ar = Ph and Tol) complexes. Twelve complexes have been structurally characterized by single crystal X-ray diffraction and shown to adopt a typical trigonal bipyramidal geometry in which the three tolyl ligands occupy the equatorial plane. NMR studies on two illustrative examples indicate that the complexes are stable in D2O and DMSO but only have a half-life of 1.2 hours in culture medium, with glucose being a contributing factor in decomposition and reduction to Bi(Tol)3. Despite their short lifetime many complexes show significant toxicity towards promastigotes at low concentration (3(O2CC6H3(2-OH,5-C6H3(2,4-F2)))2] and 838 for [Bi(m-Tol)3(O2CC6H4(2-OAc))2]. Best activity and selectivity is observed with complexes containing o- and m-tolyl ligands, and it appears the primary influence on fibroblast toxicity is the Ar ligand while the carboxylate influences promastigote toxicity. The complexes are less effective in vitro against the parasite amastigotes, where longer incubation times and harsher chemical and biological environments are encountered in the assay. Nevertheless, there were some statistically relevant differences at 1 μM against the positive controls with the best performing complexes being [Bi(o-Tol)3(O2CC6H4(2-EtO))2] and [Bi(m-Tol)3(O2CC6H4(2-OAc))2].
Synthesis of highly functionalized diaryl ethers by copper-mediated O-arylation of phenols using trivalent arylbismuth reagents
Crifar, Cynthia,Petiot, Pauline,Ahmad, Tabinda,Gagnon, Alexandre
, p. 2755 - 2760 (2014/03/21)
Highly functionalized diaryl ethers were prepared by copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes. The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported. Highly functionalized diaryl ethers were prepared by a copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes (see scheme). The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported. FG=functional group.
Palladium(II)-catalyzed aryl coupling of triarylbismuthines under air
Ohe, Toshiyuki,Tanaka, Takumi,Kuroda, Masashi,Cho, Chan Sik,Ohe, Kouichi,Uemura, Sakae
, p. 1851 - 1855 (2007/10/03)
Triarylbismuthines readily reacted with a catalytic amount of palladium(II) acetate in methanol under air to give the corresponding biaryls in high yields. The presence of oxygen was indispensable for this catalytic coupling, biaryl formation being quite slow under nitrogen. Oxygen absorption was observed during the reaction and a Pd-oxygen complex prepared separately worked effectively as a reagent for this coupling even under inert gas.
Fourier-transform Raman and infrared spectra and normal coordinate analysis of the triphenyl compounds and their methyl-, methoxy- and fluoro-substituted derivatives of arsenic, antimony and bismuth
Ludwig,Dolny,Goetze
, p. 2363 - 2372 (2007/10/03)
The Fourier transform (FT)-Raman and infrared (IR) spectra of triphenyl-, perdeuterated triphenyl-, tris(2-methylphenyl)-, tris(3-methylphenyl)-, tris(2,4,6-trimethylphenyl)-, tris(2-methoxyphenyl)-, tris(3-methoxyphenyl)-, tris(3-fluorophenyl)- and tris(
