Gold-catalyzed cyclotrimerization of arynes for the synthesis of triphenylenes

P-Arylation of Dialkyl Phosphites and Secondary Phosphine Oxides with Arynes

“…With the above background and our recent investigations on the behaviors of arynes, we became interested in studying transition-metal-free P-arylation of organophosphorus compounds under mild conditions. Arynes undergo facile insertion into various σ-bonds for the formation of carbon–carbon and carbon–heteroatom bonds due to the strong electrophilicity of the highly strained carbon–carbon triple bond. , Recently, various transition-metal-free C–P bond formation reactions via arynes have been well-developed. − In 2010, Jugé and co-workers reported an arylation of phosphines with arynes generated in situ from 2-(trimethylsilyl)­aryl triflates (Kobayashi precursors) for the synthesis of quaternary and P-stereogenic phosphonium triflates (Scheme a) .…”

Diels–Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects

“…The cyclotrimerization of arynes to phenanthrene-fused-benzyne was also described [171]. Multiple examples of applications of benzyne, bis-benzyne, arynes, and bis-and polyarynes in the synthesis of PAHs, including functionalized ones, via cycloaddition, double-cycloaddition, cyclotrimerization, and other reactions are described in the literature [37,163,[171][172][173][174]. It should be added that there are a lot of publications devoted to the synthesis of various nanographenes in the literature, including star-shaped and functionalized ones from different arynes.…”

“…Synthesis of naphthoperylene derivatives via HDDA cascade reactions [175]. Reagents and conditions: (a) CHCl3, 85 °C, ~12 h; Y = 31% (175) and 46% (174).…”

Copper-Catalyzed Addition of H–P(O) Bonds to Arynes

“…To the best of our knowledge, transition-metal-catalyzed additions of a H–P­(O) bond to in situ generated arynes remain unexplored. With our recent studies on the behaviors of arynes, , we have been interested in studying the addition of H–P­(O) bonds to arynes catalyzed by the cheaper copper salts. Herein, we report that the utilization of CuI as the catalyst for the P-arylation of secondary phosphine oxides with arynes provides a convenient and general approach to arylphosphine oxides at room temperature.…”