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Palladium-Catalyzed Annulation of Phenazastannines with 9‑(Dibromomethylene)fluorene and -(thio)xanthenes: Facile Synthesis of Acridine Moiety-Containing Bis(tricyclic) Aromatic Enes

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journal contribution
posted on 17.07.2019, 16:03 by Masaki Shimizu, Kenta Nishimura, Mizuki Mineyama, Haruka Fuji
Growing interest has been paid to bis­(tricyclic) aromatic enes as key components of functional organic materials such as molecular switches and charge-transporting materials. Currently, the synthetic approaches to the overcrowded alkenes are limited to McMurry coupling and Barton–Kellog olefination. This communication reports that palladium-catalyzed double cross-coupling reaction of phenazastannines with 9-(dibromomethylene)­fluorene, -xanthene, -thioxanthene, and -thioxanthene-S,S-dioxide serves as a facile synthetic approach to bis­(tricyclic) aromatic enes such as 9-(9H-fluoren-9-ylidene)­acridines, 9-(9H-oxanthen-9-ylidene)­acridines, 9-(9H-thioxanthen-9-ylidene)­acridines, and 9-(10,10-dioxido-9H-thioxanthen-9-ylidene)­acridines.