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

Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3651-3655. doi: 10.1002/anie.201712783. Epub 2018 Mar 1.

Abstract

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 Bu3 Sn-substituted phenalene, benzanthrene, and olympicene derivatives. Subsequent reactions with electrophiles provided synthetic access to previously inaccessible functionalized polyaromatic compounds.

Keywords: alkyne benzannulation; cyclization; polyaromatic compounds; radical reactions; zigzag edge.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.