Merging Photoredox with Palladium Catalysis: Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids under Mild Reaction Conditions

Abstract

A room temperature decarboxylative ortho-acylation of acetanilides with α-oxocarboxylic acids has been developed via a novel Eosin Y with Pd dual catalytic system. This dual catalytic reaction shows a broad substrate scope and good functional group tolerance, and an array of ortho-acylacetanilides can be afforded in high yields under mild conditions.

Recent advances in dual transition metal–visible light photoredox catalysis

“…51 At room temperature in this organic dye pohotocatalyzed setup, α-oxocarboxylic acids decarboxylatively generated the acyl radicals, which added to the palladium center. In 2016, the same research group continued the development of the organic dye photocatalysed decarboxilative C-H bond activation reactions (Figure 16).…”

Enhancing Ru(II)‐Catalysis with Visible‐Light‐Mediated Dye‐Sensitized TiO2 Photocatalysis for Oxidative C−H Olefination of Arene Carboxylic Acids at Room Temperature

“…However, less abundance and high cost of these catalysts are the major issues towards their broad utility. Organic dyes are also found ineffective and only sporadic examples are reported in this direction . Thus, the introduction of readily available inexpensive photo‐redox catalysts with good chemical stability can fulfil the available synthetic space in metallaphotoredox catalyzed C−H bond activation reactions.…”

Organic Reactions Promoted by Metal-Free Organic Dyes Under Visible Light Irradiation

“…Eosin Y (EY) is the typical organic dye to induce the synthetically useful photoredox transformations [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]. EY that absorbed visible light populates in the lowest excited singlet state.…”