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C-H arylation of triphenylene, naphthalene and related arenes using Pd/C.

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 ?-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.

SUBMITTER: Collins KD

PROVIDER: S-EPMC5649329 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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C-H arylation of triphenylene, naphthalene and related arenes using Pd/C.

Collins Karl D KD Honeker Roman R Vásquez-Céspedes Suhelen S Tang Dan-Tam D DD Glorius Frank F

Chemical science 20141222 3

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 ...[more]

PMID: 29308135

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