Organophotoredox-catalyzed cyanoalkylation of 1,4-quinones

Abstract

A visible-light-induced metal-free cyanoalkylation of 1,4-quinones under mild and redox-neutral conditions is described. This reaction proceeds at room temperature without the need of extra base or additive and is suitable...

Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters

“…In 2022, a radical tandem functionalization of 1,4-quinones 198 through cyanoalkylation was revealed by Akondi and Mainkar’s group to afford a series of cyanoalkylated quinone derivatives 199 at room temperature in the absence of a transition metal catalyst ( Scheme 31 ) [ 89 ]. A range of substituted 1,4-quinones 198 smoothly served as the coupling partners with cycloketone oxime esters 2 , in the presence of 2 mol% Rose Bengal, affording cyanoalkylated quinone derivatives 199 in moderate yields.…”

An Iron‐Catalyzed Three‐Component Radical Cascade Cyclization to Access Cyanoalkylsulfonyl Quinolino‐Quinazolinones

“…As part of our ongoing research in the field of ferrocene catalyzed deconstructive utilization of cycloketone esters [10] and inspired by notable advances in the use of hydroxylamine derivatives as radical sources to construct valuable products, [11] we explored this radical cascade cyclization by selecting the model substrates quinazolinone 1 a and oxime ester 2 a. Encouragingly, upon heating a 0.1 M CH 3 CN (ACN) solution containing these reagents, along with DABCO. (SO 2 ) 2 (DABSO) and 5 mol% Cp 2 Fe, to 60 °C for 12 hours, the three-component product 3 aa was obtained in a 38% yield (Table 1, entry 1).…”