622-47-9Relevant articles and documents
A mild and efficient carboxylate-directed C-H arylation of aryl carboxylic acids with iodobenzenes in water
Xu, Zhongmiao,Yang, Ting,Lin, Xichen,Elliott, John D.,Ren, Feng
, p. 475 - 477 (2015)
An efficient and environmental friendly Pd-catalyzed carboxylate-directed C-H arylation reaction of aryl carboxylic acids with iodobenzenes has been developed in water where Tween 20 was added (2% w/w) to form aqueous micelles to increase the solubility of starting materials. In this aqueous protocol, the reactions proceeded at a lower temperature (80 °C) compared with the traditional procedures using organic solvents (100 °C and above) and wide substrate scopes were demonstrated (15 examples, 62-92% yields).
The thiol-based reduction of Bi(V) and Sb(V) anti-leishmanial complexes
Duffin, Rebekah N.,Stephens, Liam J.,Blair, Victoria L.,Kedzierski, Lukasz,Andrews, Philip C.
, (2021/05/10)
Low molecular weight thiols including trypanothione and glutathione play an important function in the cellular growth, maintenance and reduction of oxidative stress in Leishmania species. In particular, parasite specific trypanothione has been established as a prime target for new anti-leishmania drugs. Previous studies into the interaction of the front-line Sb(V) based anti-leishmanial drug meglumine antimoniate with glutathione, have demonstrated that a reduction pathway may be responsible for its effective and selective nature. The new suite of organometallic complexes, of general formula [MAr3(O2CR)2] (M = Sb or Bi) have been shown to have potential as new selective drug candidates. However, their behaviour towards the critical thiols glutathione and trypanothione is still largely unknown. Using NMR spectroscopy and mass spectrometry we have examined the interaction of the analogous Sb(V) and Bi(V) organometallic complexes, [SbPh3(O2CCH2(C6H4CH3))2] S1 and [BiPh3(O2CCH2(C6H4CH3))2] B1, with the trifluoroacetate (TFA) salt of trypanothione and L-glutathione. In the presence of trypanothione or glutathione at the clinically relevant pH of 4–5 for Leishmania amastigotes, both complexes undergo facile and rapid reduction, with no discernible difference. However, at a higher pH (6–7), the complexes behave quite differently towards glutathione. The Bi(V) complex is again reduced rapidly but the Sb(V) complex undergoes slow reduction over 8 h (t1/2 = 54 min.) These results give the first insights into why the highly oxidising Bi(V) complexes display low selectivity in their cytotoxicity towards leishmanial and mammalian cells, while the Sb(V) complexes show good selectivity.
Relative activity of metal cathodes towards electroorganic coupling of CO2 with benzylic halides
Engelhardt, Helen,Klinkova, Anna,Medvedev, Jury J.,Medvedeva, Xenia V.
, (2021/05/26)
Electrochemical reduction of benzylic halides represents a convenient route to generating carbanions for their subsequent coupling with CO2 to obtain various carboxylic acids. Despite the industrial prospects of this synthetic process, it still lacks systematic studies of the efficient catalysts and reaction media design. In this work, we performed a detailed analysis of the catalytic activity of a series of different metal electrodes towards electroreduction of benzylic halides to corresponding radicals and carbanions using cyclic voltammetry. Specifically, we screened and summarized the performance of 12 bulk metal cathodes (Ag, Au, Cu, Pd, Pt, Ni, Ti, Zn, Fe, Al, Sn, and Pb) and 3 carbon-based materials (glassy carbon, carbon cloth, and carbon paper) towards electrocarboxylation of eight different benzylic halides and compare it to direct CO2 reduction in acetonitrile. Extensive experimental studies along with a detailed analysis of the results allowed us to map specific electrochemical properties of different metal electrodes, i.e., the potential zones related to the one- and two-electron reduction of organic halides as well as the potential windows where the electrochemical activation of CO2 does not occur. The reported systematic analysis should facilitate the development of nanostructured electrodes based on group 10 and 11 transition metals to further optimize the efficiency of electrocarboxylation of halides bearing specific substituents and make this technology competitive to current synthetic methods for the synthesis of carboxylic acids.
