Radical Alkyne peri‐Annulation Reactions for the Synthesis of Functionalized Phenalenes, Benzanthrenes, and Olympicene

• Published in: Angewandte Chemie International Edition Vol. 57; no. 14; pp. 3651 - 3655
• Main Authors: Tsvetkov, Nikolay P., Gonzalez‐Rodriguez, Edgar, Hughes, Audrey, dos Passos Gomes, Gabriel, White, Frankie D., Kuriakose, Febin, Alabugin, Igor V.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 26.03.2018; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: alkyne benzannulation; Alkynes; Chemical reactions; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; cyclization; Organic chemistry; Physical Sciences; polyaromatic compounds; radical reactions; Science & Technology; Substrates; zigzag edge; polyaromatic compounds; ARENES; radical reactions; BENZANNULATIONS; RAPID ACCESS; alkyne benzannulation; PHOTOPHYSICAL PROPERTIES; cyclization; HEXABENZOCORONENE; TRACELESS DIRECTING GROUPS; zigzag edge; PI-EXTENSION; FUSED HELICENES; NANOGRAPHENES; CATALYZED HYDROARYLATION
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201712783

Radical cyclization reactions at a peri position were used for the synthesis of polyaromatic compounds. Depending on the choice of reaction conditions and substrate, this flexible approach led to Bu3Sn‐substituted phenalene, benzanthrene, and olympicene derivatives. Subsequent reactions with electrophiles provided synthetic access to previously inaccessible functionalized polyaromatic compounds. peri useful: Radical cyclization reactions at a peri position were used for the synthesis of polyaromatic compounds. Depending on the choice of reaction conditions and substrate, this flexible approach led to Bu3Sn‐substituted phenalene, benzanthrene, and olympicene derivatives (see scheme). Subsequent reactions with electrophiles provided synthetic access to previously inaccessible functionalized polyaromatic compounds.