723259-89-0Relevant academic research and scientific papers
Erratum: Catalytically Relevant Intermediates in the Ni-Catalyzed C(sp2)-H and C(sp3)-H Functionalization of Aminoquinoline Substrates (J. Am. Chem. Soc. (2019) 141:43 (17382-17387) DOI: 10.1021/jacs.9b09109)
Bour, James R.,Kampf, Jeff W.,Roy, Pronay,Sanford, Melanie S.
supporting information, p. 14021 - 14021 (2021/09/08)
Further analysis of our data revealed that the thermolysis ofNi(III) complex 4b does not lead to C(sp3)-N bondformingreductive elimination to form ?-lactam 3b-H. As such, our claim that this is “the first directly observable example of C(sp3)-N coupling from an isolated NiIII center” is incorrect. Equation 6 should be modified as follows: As a consequence, the statement in the Abstract that “a NiIII s-alkyl analogue underwent C(sp3)-N bond-forming reductive elimination at 140 °C in DMF to afford a ?-lactam product” is also incorrect. The TOC graphic should also be corrected as follows: After the discovery of this major error, we went back and carefully repeated all of the synthesis and reactivity experiments described in the Article to ensure their accuracy and reproducibility. This has led to changes in the yields and in some cases solvent and reaction time for many of the reactions reported therein. The Supporting Information has been updated with revised procedures and spectra as well as updated yields. In addition, we have included in the revised Supporting Information a copy of an updated manuscript with each change highlighted to clearly indicate these revisions. Unlike the error in eq 6, none of these additional changes alters our key conclusions from the original manuscript.FF
Catalytically Relevant Intermediates in the Ni-Catalyzed C(sp2)-H and C(sp3)-H Functionalization of Aminoquinoline Substrates
Roy, Pronay,Bour, James R.,Kampf, Jeff W.,Sanford, Melanie S.
, p. 17382 - 17387 (2019/11/03)
This Article describes the synthesis and characterization of cyclometalated aminoquinoline NiII σ-aryl and σ-alkyl complexes that have been proposed as key intermediates in Ni-catalyzed C-H functionalization reactions. These NiII complexes serve as competent catalysts for the C-H functionalization of aminoquinoline derivatives with I2. They also react stoichiometrically with I2 to form either aryl iodides or β-lactams within minutes at room temperature. Furthermore, they react with AgI salts at -30 °C to afford isolable five-coordinate NiIII species. The NiIII σ-aryl complexes proved inert toward C(sp2)-I bond-forming reductive elimination under all conditions examined (up to 140 °C in DMF). In contrast, a NiIII σ-alkyl analogue underwent C(sp3)-N bond-forming reductive elimination at 140 °C in DMF to afford a β-lactam product. However, despite the ability of this latter NiIII species to participate in stoichiometric product formation, the complex was not a competent catalyst for β-lactam formation. Overall, these results suggest against the intermediacy of NiIII species in these C-H functionalization reactions.
CoIII-Catalyzed Isonitrile Insertion/Acyl Group Migration Between C?H and N?H bonds of Arylamides
Kalsi, Deepti,Barsu, Nagaraju,Sundararaju, Basker
supporting information, p. 2360 - 2364 (2018/02/22)
A general efficient and site-selective cobalt-catalyzed insertion of isonitrile into C?H and N?H bonds of arylamides through C?H bond activation and alcohol assisted intramolecular trans-amidation is demonstrated. This straightforward approach overcomes the limitation by the presence of strongly chelating groups. Isolation of CoIII-isonitrile complex B has been achieved for the first time to understand the reaction mechanism.
Nickel(II)-Mediated Regioselective C H Monoiodination of Arenes and Heteroarenes by using Molecular Iodine
Khan, Bhuttu,Kant, Ruchir,Koley, Dipankar
, p. 2352 - 2358 (2016/07/28)
The 8-aminoquinoline-directed, nickel(II)-mediated ortho-iodination of benzamides using molecular iodine has been developed. The process is highly regioselective and furnishes only monoiodinated products. A broad range of arenes and heteroarenes with diverse functional groups provided monoiodinated products in good to excellent yields. (Figure presented.) .
Design and preparation of aza-analogues of benzo[c]phenanthridine framework with cytotoxic and antiplasmodial activities
Yapi, Ange-Désiré,Desbois, Nicolas,Chezal, Jean-Michel,Chavignon, Olivier,Teulade, Jean-Claude,Valentin, Alexis,Blache, Yves
experimental part, p. 2854 - 2859 (2010/08/20)
Benzo[c]phenanthridine alkaloids represent interesting lead for the discovery of new potential antiplasmodial and/or anticancer drugs. In this field, a novel library of aza-analogs of benzo[c]phenanthroline framework derivatives was designed and prepared. Although these compounds did not have specific antiplasmodial activities, some of them displayed specific in vitro activity against two cancer lines especially compound 24 with an IC50 against the MCF7 line of 0.6 μM.
