A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides. Issue 11 (14th September 2016)

• Record Type: Journal Article
• Authors: Seifert, Sabine; Schmidt, David; Würthner, Frank
• Is Part Of: Organic chemistry frontiers. Volume 3:Issue 11(2017:Nov.)
• Page Start: 1435
• Page End: 1442
• Publication Date: 2016-09-14
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00421k
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A novel synthetic strategy based on cascade C–C cross-coupling and C–H arylation afforded structurally unique polycyclic aromatics with desirable optical and redox properties. Abstract : Herein we report a synthetic method to annulate naphthalimide moieties at different positions of a pyrene core by a cascade reaction involving palladium-mediated Suzuki–Miyaura cross-coupling and direct C–H arylation affording a new class of rylene bisimides, which we term as pseudo -rylene bisimides. The Pd-mediated reactions of peri -dibromonaphthalimide and pyrene boronic acid esters lead exclusively to six-membered ring annulation by a cascade C–C bond formation, for which a mechanistic rationale is proposed. Depending on the molecular geometry of the new pseudo -rylene bisimides, their optical properties resemble those of zethrene or terrylene bisimides, or polycyclic aromatic hydrocarbons like coronenes. The structural integrity of this new type of pseudo -rylene bisimides was confirmed by single crystal X-ray analysis.