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)
-
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.
TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides
Singh, Garima,Dada, Ravikrishna,Yaragorla, Srinivasarao
supporting information, p. 4424 - 4427 (2016/09/13)
A One-Pot tandem Schmidt–Ritter process for the synthesis of amides has been developed using the super acid as catalyst. The in situ generated aryl/aliphatic nitriles from the reaction of aldehydes and sodium azide in the presence of TfOH and AcOH (Schmidt reaction) react with suitable alcohol (Ritter reaction) to give the amides. For the first time we observed that during the Schmidt process N-acylimides were generated along with nitriles, interestingly these N-acylimides also participated in the Ritter reaction.
