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Issue 3, 2015
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C–H arylation of triphenylene, naphthalene and related arenes using Pd/C

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Abstract

A highly selective arylation of a number of polyaromatic hydrocarbons (PAHs) with aryliodonium salts and Pd/C as the only reagent is reported. The first C–H functionalization of triphenylene is explored, and proceeds at the most sterically hindered position. This non-chelate assisted C–H functionalization extends the reactivity profile of Pd/C and provides controlled access to π-extended PAHs, an important aspect of work towards the preparation of nanographenes. Mechanistic studies suggest in situ formation of catalytically active insoluble nanoparticles, and that the reaction likely proceeds via a Pd(0)/Pd(II) type reaction manifold.

Graphical abstract: C–H arylation of triphenylene, naphthalene and related arenes using Pd/C

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Publication details

The article was received on 04 Oct 2014, accepted on 19 Dec 2014 and first published on 22 Dec 2014


Article type: Edge Article
DOI: 10.1039/C4SC03051F
Citation: Chem. Sci., 2015,6, 1816-1824
  • Open access: Creative Commons BY license
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    C–H arylation of triphenylene, naphthalene and related arenes using Pd/C

    K. D. Collins, R. Honeker, S. Vásquez-Céspedes, D. D. Tang and F. Glorius, Chem. Sci., 2015, 6, 1816
    DOI: 10.1039/C4SC03051F

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