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Sökning: WFRF:(Ahlburg A.)

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1.
  • Antonacci, G., et al. (författare)
  • Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism
  • 2017
  • Ingår i: European Journal of Organic Chemistry. - : Wiley. - 1434-193X. ; :32, s. 4758-4764
  • Tidskriftsartikel (refereegranskat)abstract
    • The substrate scope and the mechanism have been investigated for the MnCl2-catalyzed cross-coupling reaction between aryl halides and Grignard reagents. The transformation proceeds rapidly and in good yield when the aryl halide component is an aryl chloride containing a cyano or an ester group in the para position or a cyano group in the ortho position. A range of other substituents gave no conversion of the aryl halide or led to the formation of side products. A broader scope was observed for the Grignard reagents, where a variety of alkyl- and arylmagnesium chlorides participated in the coupling. Two radical-clock experiments were carried out, and in both cases an intermediate aryl radical was successfully trapped. The cross-coupling reaction is therefore believed to proceed by an S(RN)1 mechanism, with a triorganomanganate complex serving as the most likely nucleophile and single-electron donor. Other mechanistic scenarios were excluded based on the substrate scope of the aryl halide.
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2.
  • Santilli, C., et al. (författare)
  • The Manganese-Catalyzed Cross-Coupling Reaction and the Influence of Trace Metals
  • 2017
  • Ingår i: European Journal of Organic Chemistry. - : Wiley. - 1434-193X. ; 2017:35, s. 5269-5274
  • Tidskriftsartikel (refereegranskat)abstract
    • The substrate scope of the MnCl2-catalyzed cross-coupling between aryl halides and Grignard reagents has been extended to several methyl-substituted aryl iodides by performing the reaction at elevated temperature in a microwave oven. A radical clock experiment revealed the presence of an aryl radical as an intermediate leading to the proposal of an SRN1 pathway for the coupling. The mechanistic information gave rise to suspicion about two previously published cross-coupling reactions catalyzed by manganese(II) salts. As a result, the coupling between aryl halides and organostannanes as well as between aryl halides and amines were revisited. Both reactions were found impossible to reproduce without the addition of small amounts of palladium or copper and are therefore not believed to be catalyzed by manganese. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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  • Resultat 1-2 av 2
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tidskriftsartikel (2)
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refereegranskat (2)
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Norrby, Per-Ola, 196 ... (2)
Fristrup, P (2)
Antonacci, G. (2)
Ahlburg, A. (2)
Madsen, R. (2)
Santilli, C. (1)
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Beigbaghlou, S. S. (1)
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Göteborgs universitet (2)
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Engelska (2)
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2017 (2)

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