1118-32-7Relevant articles and documents
Size-selective olefin hydrogenation by a Pd nanocluster provided in an apo-ferritin cage
Ueno, Takafumi,Suzuki, Masako,Goto, Toshiaki,Matsumoto, Tomoharu,Nagayama, Kuniaki,Watanabe, Yoshihito
, p. 2527 - 2530 (2004)
Deep penetration by substrates through the size-restricted channels of an apoferritin cage results in size-selective olefin hydrogenation at the Pd nanocluster core (see picture). The encapsulated zero-valent cluster is synthesized in situ by chemical reduction of PdII ions in the apoferritin cage.
Mechanistic evidence for intermolecular radical carbonyl additions promoted by samarium diiodide
Hansen, Anna Mette,Lindsay, Karl B.,Sudhadevi Antharjanam,Karaffa, Jakob,Daasbjerg, Kim,Flowers II, Robert A.,Skrydstrup, Troels
, p. 9616 - 9617 (2006)
In this work, mechanistic studies were performed to understand the SmI2/H2O-mediated coupling of N-acyl oxazolidinones with acrylates and acrylamides, providing γ-keto esters and amides, respectively. Our results provide experimental evidence that C-C bond formation via intermolecular radical addition reactions to carbonyl substrates can be promoted by samarium diiodide. Coupling reactions with N-cyclopropylcarbonyl-2-oxazolidinone suggest the α,β-unsaturated esters/amides are reduced by the low-valent lanthanide reagent and not the N-acyl oxazolidinones, as originially proposed (J. Am. Chem. Soc. 2005, 127, 6544). Rate measurements support the preferred reduction of an acrylate or acrylamide by SmI2/H2O in the presence of an N-acyl oxazolidinone. In the absence of the N-acyl oxazolidinone, SmI2/H2O promotes dimerization of the acrylates, whereas the C=C bond of the acrylamides is reduced. In addition, coupling of the Pfp ester of Cbz-protected phenylalanine with an acrylamide leads only to reduction of the acrylamide and recovered ester, whereas the same coupling with the N-acyl oxazolidinone derivative provides the γ-keto amides. These results imply that a pathway involving nucleophilic acyl substitution cannot take place and that a radical mechanism must be invoked to explain the C-C bond formation. We propose that the acrylate/acrylamide is reduced to a conjugated ketyl radical that adds to the exocyclic carbonyl group of the N-acyl oxazolidinone, activated through bidentate coordination to a lanthanide ion. Copyright
Synthesis of N-tert-butyl amides by reaction of tert-butyl bromide with amides in the presence of manganese compounds
Khusnutdinov,Shchadneva,Khisamova
, p. 1502 - 1504 (2015)
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Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides
Li, Qiao,Jin, Hongwei,Liu, Yunkui,Zhou, Bingwei
, p. 3466 - 3472 (2020)
We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.
Homoleptic zirconium amidates: Single source precursors for the aerosol-assisted chemical vapour deposition of ZrO2
Catherall, Amanda L.,Hill, Michael S.,Johnson, Andrew L.,Kociok-K?hn, Gabriele,Mahon, Mary F.
supporting information, p. 10731 - 10739 (2016/11/29)
We report the development of a true single source precursor (i.e. without any need for an exogenous source of oxygen) for the growth of zirconia thin films by aerosol-assisted chemical vapour deposition (AACVD) using an original family of zirconium(iv) amidate derivatives, which are easily prepared by protonolysis of [Zr(NMe2)4] with the free amide pro-ligands. In all but one case the reactions resulted in the isolation of the corresponding homoleptic eight-coordinate zirconium(iv)tetrakis(amidato) derivatives. Three of these species along with a tris(amidato)dimethylamido zirconium(iv) derivative have been characterised by single crystal X-ray diffraction analysis. The materials potential of the homoleptic compounds was identified through the application of design criteria derived from consideration of the existing knowledge base relating to the pyrolysis of wholly organic amides. In this manner the thermal decomposition of the homoleptic derivatives benefits from facile, molecularly imposed pyrolysis pathways, which provide for the privileged generation of volatile small molecule by-products and the production of contaminant-free solid oxide material. Thermogravimetric analysis, in conjunction with NMR spectroscopic analysis of the volatile products resulting from their thermal decomposition, indicated the potential of the homoleptic species as exquisite single source precursors to ZrO2 at moderate temperatures. The compound bearing both N- and C-iso-propyl substituents was, thus, applied as a true single source precursor under ambient pressure AACVD conditions. The resultant films, deposited on either SiO2-coated glass or quartz substrates, are smooth and comprise small and densely packed crystalline particulates that are shown by XRD to be primarily cubic ZrO2. Compositional analysis by X-ray photoelectron spectroscopy (XPS) revealed that the oxygen delivered, and the decomposition pathway provided, by the amidate ligand structure yields ZrO2 films which, though slightly sub-stoichiometric (ZrO1.8-1.9), contain undetectable levels of carbon incorporation.
Oxidative activation of dihydropyridine amides to reactive acyl donors
Funder, Erik Daa,Trads, Julie B.,Gothelf, Kurt V.
supporting information, p. 185 - 198 (2015/01/16)
Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields. This journal is
