Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids Driven by Visible Light and Using Molecular Oxygen

Abstract

This paper discloses the first example of photocatalytic direct decarboxylative hydroxylation of carboxylic acids. It enables the conversion of a variety of readily available carboxylic acids to alcohols in moderate to high yields. This unprecedented protocol is accomplished under extremely mild reaction conditions using molecular oxygen (O2) as a green oxidant and using visible light as a driving force.

Decarboxylative Giese‐Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox‐Neutral Protocol

“…To our delight, when the reaction was performed under air, it was complete after only 17 h (entry 1). Surprisingly, performance of the reaction under argon (entry 9) had an even more deleterious effect on the yield than when the reaction was performed under oxygen (entry 10) . Regarding the stoichiometry, a slight excess of acid (1.5 equiv.)…”

Decarboxylative Oxygenation via Photoredox Catalysis

“…[7,8] In addition, Song et al have shown that secondary benzylic alcohols can be generated via radical decarboxylative oxygenation, followed by reductive work up. [9] Despite these advances, a general method for decarboxylative oxygenation, which is selective for the carbonyl product, has not yet been described. Herein, we present a broadly applicable decarboxylative oxygenation protocol, enabling the synthesis of ketones, aldehydes, and amides directly from a diverse range of aliphatic carboxylic acids.…”

Photoredox‐Catalyzed Decarboxylative Oxidation of Arylacetic Acids

“…tion of arylacetic acids has been underdeveloped. [6] Herein, we report an ew methodt oa ccess aryl-aldehydes,-ketones, and -carboxylic acids through photoredox-catalyzed decarboxylation of arylacetic acids (Figure 1b). Ther eaction occursu nder mild conditions (40 8Cu nder open air), thereby tolerating a wide range of functional groups.…”