Visible‐Light‐Mediated Aerobic Oxidative C(sp³)−C(sp³) Bond Cleavage of Morpholine Derivatives Using 4CzIPN as a Photocatalyst

Abstract

Herein, a metal‐free strategy for the aerobic oxidative cleavage of the inert C(sp3)−C(sp3) bond was developed. Deconstruction of morpholine derivatives was conducted using visible light as an energy source and O2 as an oxidant under mild conditions. This procedure demonstrated suitable selectivity and functional group tolerance. Moreover, a possible mechanism involving a radical process was proposed based on a series of mechanism exploration and control experiments.

Photocatalyzed Oxygenation Reactions with Organic Dyes: State of the Art and Future Perspectives

“…However, the high dissociation bond energy and the stability of C-C bonds make this process challenging, and, in general, the use of a metalbased catalyst is needed [69]. 4CzIPN was recently studied as an organic photocatalyst for the selective C-C bond oxidative cleavage (Scheme 16) [70]. In this study, 29 N-aryl morpholine derivatives were tested, showing low to good yields (13-83%) but significant functional group tolerance.…”

“…However, the high dissociation bond energy and the stability of C-C bonds make this process challenging, and, in general, the use of a metal-based catalyst is needed [69]. 4CzIPN was recently studied as an organic photocatalyst for the selective C-C bond oxidative cleavage (Scheme 16) [70].…”

“…However, the high dissociation bond energy and the stability of C-C bonds make this process challenging, and, in general, the use of a metalbased catalyst is needed [69]. 4CzIPN was recently studied as an organic photocatalyst for the selective C-C bond oxidative cleavage (Scheme 16) [70]. Reactions were carried out in water, and added-value carbonyl products were obtained with good to excellent yields (40-95%) in 48 h. In addition, reactions could be efficiently scaled up on a gram-scale; 1,1-diphenylethylene was converted to benzophenone In this study, 29 N-aryl morpholine derivatives were tested, showing low to good yields (13-83%) but significant functional group tolerance.…”

Deep-blue emission and thermally activated delayed fluorescence via Dimroth rearrangement of tris(triazolo)triazines

“…1,8 In recent years, the applications of TADF materials have grown beyond display technology, most notably to encompass time-gated biological imaging [9][10][11][12][13][14] and organo-photocatalysis. [15][16][17][18][19] To further encourage the mainstream adoption of TADF materials in both biology and chemistry, new donor-acceptor motifs displaying TADF remain critical to furthering emitter design and practical applications.…”

Lewis Acid-Promoted Oxidative Cleavage of Carbon–Carbon Bonds: Synthesis of N-Arylated Lactam-Type Iminosugars

“…In recent years, many new effective methods have been successfully found for the oxidative cleavage of carbon–carbon bonds of amines, such as photocatalytic or Lewis acid-catalyzed oxidative cleavage of piperazine, morpholine derivatives, and so on (Scheme a–c). For example, Zhou and Dong et al studied the oxidative cleavage of carbon–carbon single bond in N -arylated/ N -alkylated piperazine or morpholine derivatives in the presence of O 2 under visible light induction through SET (single-electron transfer) mechanism . Beller and co-workers used Lewis acids as catalysts and air as the ideal oxidant to achieve the oxidative cleavage of N- substituted piperazine or morpholine derivatives .…”