Ru(ii)-Catalyzed C–H addition and oxidative cyclization of 2-aryl quinazolinones with activated aldehydes

Abstract

The ruthenium(II)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes is described. The method enables the site‐selective hydroxyalkylation under redox-neutral conditions. Moreover, this protocol provides a facile access to various...

Catalyst-Controlled C–H Allylation and Annulation of 2-Aryl Quinazolinones with 2-Methylidene Cyclic Carbonate

“…C–H olefination and intramolecular aza-Michael reactions were also reported under Ru­(II) or Rh­(III) catalysis . Intramolecular annulation could be achieved by the coupling reaction between 2-aryl quinazolinones and aldehydes to deliver tertiary alcohols …”

Ruthenium(II)-Catalyzed Grignard-Type Nucleophilic Addition of C(sp2)–H Bonds to Unactivated Aldehydes

“…Recently, reactions of C­(sp 2 )–H bonds with aldehydes catalyzed by transition metals such as Rh, Ru, , Co, and Mn have been extensively developed. However, for the high-oxidation-state transition metal catalysts, due to the low nucleophilicity of the C–M bond and reversibility of aldehyde insertion into the C–M bond, all reports up to now are limited to the active aldehydes such as formaldehyde, ethyl glyoxylate, and aromatic aldehydes with electron-withdrawing groups (Scheme a).…”

Dimeric Manganese-Catalyzed Direct Nucleophilic Addition of C(sp2)–H Bonds to Inert Aldehydes

“…Because of the low nucleophilicity of the C–M bond formed by C–H activation and the reversibility of aldehyde insertion into the C–M bond, the reactions of C­(sp 2 )–H bonds with aldehydes catalyzed by transition metals such as Rh, Ru, , Co, and Mn are mainly limited to the active aldehydes such as formaldehyde, ethyl glyoxylate, and aromatic aldehydes with electron-withdrawing groups (Scheme a). The Mn­(CO) 5 Br-catalyzed nucleophilic addition of C­(sp 2 )–H bonds to unactivated aldehydes was first reported by Kuninobu, Takai, and coworkers in 2007, with the assistance of HSiEt 3 to afford the corresponding silyl ether .…”