Arynes in the synthesis of polycyclic aromatic hydrocarbons

Abstract

Polycyclic aromatic hydrocarbons are of great interest as a result of their self-assembly properties and 5 excellent charge-transfer abilities. They are therefore promising candidates for organic semiconducting devices. In order to develop better optoelectronic devices, chemists have made considerable effort to investigate synthetic methods for polycyclic aromatic hydrocarbons. Among many building blocks, arynes are a promising reactive intermediate for the construction of polycyclic aromatic hydrocarbons and so has been studied over many decades. In this review, we will summarize recent progress on the 10 construction of polycyclic aromatic hydrocarbons using arynes as starting materials. Journal Name, [year], [vol], 00-00 | 7 101a R = C 6 H 13 101b R = C 8 H 17 72 102 103 45% 60% Scheme 21 65The aryne precursors shown in Scheme

New advances in nanographene chemistry

“…45,93 In particular, Perez, Guitian, Peña, and co-workers have demonstrated that the palladium-catalysed cyclotrimerization of arynes enables very efficient preparation of triphenylene 94 and a variety of its extended derivatives, 93 including hexabenzo-[a,c,g,i,m,o]triphenylene (C42), 95 hexabenzo[a,c,k,m,u,w]trinaphthylene (C54) 96 and hexabenzo[a,c,o,q,c 1 ,e 1 ]trianthrycene (C66). 45,93 In particular, Perez, Guitian, Peña, and co-workers have demonstrated that the palladium-catalysed cyclotrimerization of arynes enables very efficient preparation of triphenylene 94 and a variety of its extended derivatives, 93 including hexabenzo-[a,c,g,i,m,o]triphenylene (C42), 95 hexabenzo[a,c,k,m,u,w]trinaphthylene (C54) 96 and hexabenzo[a,c,o,q,c 1 ,e 1 ]trianthrycene (C66).…”

“…17, 25 A variety of rationally designed polyphenylene precursors have thus been ''graphitized'' through intramolecular cyclodehydrogenation to provide a number of GNRs with different widths, edge structures and heteroatom doping. 38,39 Comprehensive reviews on the bottom-up chemical syntheses of graphene molecules 9,20,23,[40][41][42][43][44][45][46][47][48] and GNRs have been reported. 37 Whereas the majority of solution-synthesized GNRs have limited solubility and thus cannot be microscopically investigated, the surface-synthesis protocol allowed in situ visualization of the entire GNR formation process with atomic resolution using scanning tunneling microscopy (STM).…”

Schwefelylide durch (3+2)‐Cycloaddition von Arinen mit Vinylsulfiden – stereoselektive Synthese hoch substituierter Alkene

“…Arine erfuhren in den letzten Jahren verstärkte Aufmerksamkeit in der organischen Chemie, auch aufgrund der Entwicklung neuer Methoden zu ihrer Herstellung . Zudem nutzen zahlreiche neue Synthesemethoden Arine als Intermediate, und auch in der Naturstoffsynthese findet die Arinchemie Anwendung . Wegen ihres tiefliegenden LUMO reagieren Arine effizient mit vielen anionischen und neutralen Nukleophilen.…”

Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-C H silylation of phenols with traceless acetal directing groups

“…Ever since the discovery of benzynes in the mid 1950s, 1 these highly reactive intermediates have been employed in a wide variety of important applications, such as the synthesis of bioactive molecules, 2 organic materials, 3 and catalysts. 4 Additionally, benzynes enable the formation of diverse heterocyclic frameworks, which are difficult to obtain by conventional methods, via reactions with various arynophiles.…”