Palladium-Catalyzed Cycloaddition Reactions of Arynes

Palladium-Catalyzed Annulation of Arynes byo-Halobenzamides: Synthesis of Phenanthridinones

“…In all cases, the cyclotrimerization side product 4a 19 and the desired benzyne annulation product 3a were observed.…”

Bottom‐up Approaches to Nanographenes through Organic Synthesis

“…This allowed us to isolate the thermodynamically unstable C 2 -symmetric conformer of hexabenzotriphenylene (15), which was structurally characterized by X-ray diffraction analysis by Bennett, Wenger, and coworkers [24]. Similarly, palladium-catalyzed [2+2+2]cycloaddition of 4,5-didehydrophenanthrene (26, Scheme 11.4) afforded double helicene 16 [25], while the regioisomeric aryne 1,2-didehydrophenanthrene (27) led to a mixture of compounds 14 and 17 [26]. Palladium-catalyzed cocyclotrimerization of two molecules of 2,3-didehydrotriphenylene (28) and benzyne (29) afforded polyarene 18 among other PAHs [27].…”

Aryne Cycloaddition Reactions in the Synthesis of Large Polycyclic Aromatic Compounds

“…Shortly after, the [2+2+2] co‐cycloaddition of benzynes with electron‐deficient alkynes was reported, and this proved to be chemoselective in allowing the preferential formation of either phenanthrenes or naphthalenes depending on the palladium catalyst employed 21. In the last decade our group and others have developed a variety of metal‐catalysed cycloaddition and annulation reactions involving arynes and these have proved to be useful for the synthesis of PACs 16d,16g…”