A Direct Arylation‐Cyclisation Reaction for the Construction of Medium‐Sized Rings. Issue 52 (7th September 2017)

• Record Type: Journal Article
• Authors: Whitaker, Daniel; Batuecas, María; Ricci, Paolo; Larrosa, Igor
• Is Part Of: Chemistry. Volume 23:Issue 52(2017)
• Page Start: 12763
• Page End: 12766
• Publication Date: 2017-09-07
• Subjects: biaryls -- C−H activation -- homogeneous catalysis -- medium-ring compounds -- organometallic chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201703527
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A strategy for assembling biaryls linked through a medium‐sized ring is herein presented. π‐Complexation of fluoroarenes to chromium tricarbonyl activates the molecule towards both C−H activation and nucleophilic aromatic substitution without covalently altering the molecular connectivity of the arene. The construction of bridged biaryl molecules with 6–10‐membered core rings is achieved through a one‐pot C−H arylation/nucleophilic aromatic substitution sequence. The methodology is applicable to the synthesis of heterocyclic as well as fully carbocyclic rings. Abstract : One‐pot, two‐step, three rings : An intermolecular cyclisation reaction has been developed, combining direct C−H arylation with nucleophilic aromatic substitution. π‐Complexation of fluoroarenes to Cr(CO)3 greatly enhances the reactivity of both steps. Rings with 6 to 10 members are accessible through cyclisation with O, N and C‐centered nucleophiles.