Decarbonylative/decarboxylative [4 + 2] annulation of phthalic anhydrides and cyclic iodoniums towards triphenylenes

Abstract

A palladium-catalyzed decarbonylative/decarboxylative [4 + 2] annulation of phthalic anhydrides with cyclic diaryliodonium salts to synthesize triphenylenes has been developed. The reaction shows good functional group tolerance with high yield...

Phthalic anhydride (PA): a valuable substrate in organic transformations

“…In 2022, the palladium-catalyzed decarbonylative/decarboxylative [4 + 2] annulation of PA ( 1 ) with cyclic diaryliodonium salt ( 85 ) to synthesize triphenylene ( 86 ) developed by Li and coworkers (Scheme 33). 138…”

Sequential annulation of bidentate diamines for modular access to N-fused/helical/spiro-carbazole scaffolds

“…11 For example, Wen 12 and Nachtsheim, 13 respectively, reported [4 + 1] annulative dual C–N coupling of anilines with cyclic diaryliodonium salts using Cu and Pd catalysis, while the reaction of ortho -substituted anilines has not been documented. Recently, our group reported the synthesis of benzo[ c ]cinnolines, 14 tribenzo[ b , d , f ]azepines, 15 and triphenylenes 16 using cyclic diaryliodonium salts. The retrosynthetic analysis of the N-fused Cz skeleton suggests that it could be accessed by intramolecular deaminative cyclization of N -aminoaryl carbazole which could be prepared from a cyclic diaryliodonium salt and a diamine (Scheme 1c).…”

Metal-free homo-/cross-anion–cation coupling of cyclic diaryl λ3-bromanes

“…Furthermore, the reaction of diaryl λ 3 -bromanes with other competitive anions in the same system remains unknown (Scheme 1c). On the basis of our ongoing interest in the hypervalent chemistry, 23 we herein report the metal-free homo anion–cation coupling of cyclic diarylbrominium tosylates with 100% atom economy for the first time (Scheme 1b). When the anions OTs, OMe, and OAc existed in one pot (Scheme 1c), the more nucleophilic anion showed higher reactivity (OMe − > OAc − > OTs − ).…”