Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones

Abstract

A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.

Transition Metal‐Catalyzed Synthesis of 1,2‐Diketones: An Overview

“…Recently, Singh and co‐workers developed an efficient photocatalytic protocol for the synthesis of 1,2‐diketones 58 from cinnamic acids 56 and aryl halides 57 in the presence of N , N′ ‐bis(2,6‐diisopropylphenyl)‐3,4,9,10‐perylenetet‐racarboxylic diimide (PDI), CuCl, TBHP, and Et 3 N in moderate to good yields (Scheme 21). This approach shows a broad substrate scope by using different substituted substrates like Me, Cl, F, CN, NO 2 , CF 3 , COOMe, and OMe to furnish the corresponding products 58 in good yields [42] …”

“…This approach shows a broad substrate scope by using different substituted substrates like Me, Cl, F, CN, NO 2 , CF 3 , COOMe, and OMe to furnish the corresponding products 58 in good yields. [42]…”

Transition metal-free, photocatalytic arylation and dioxygenation for vicinal diketone synthesis using alkynes and arene diazonium salts

“…For example, the coupling and oxygenation of styrenes with aryl halides, aryl hydrazines and arene diazonium salts with transition metal-catalysis (Scheme 1E), 13 and the coupling and oxygenation of alkynyl carboxylic acids with aryl boronic acids/aryl iodides have also been realized with Mn and Cu catalysis, respectively (Scheme 1F). 14 The reactions of terminal alkynes with aryl hydrazines have been developed for vicinal diketone synthesis with a Co/Ag co-catalytic system (Scheme 1G-I). 15…”

I2-Catalyzed Carbonylation of α-Methylene Ketones to Synthesize 1,2-Diaryl Diketones and Antiviral Quinoxalines in One Pot

“…1,2-Diaryl diketones are a vital class of organic compounds frequently found in structural units of natural products and bioactive molecules. − They are also versatile intermediates used in the synthesis of biologically active heterocyclics, such as imidazoles, − quinoxalines, − indoles, pyrazines, and triazines. − Furthermore, 1,2-diaryl diketones could be transformed into greatly important functional materials with electronic and photochemical properties. − Therefore, various traditional and modern methods for the formation of 1,2-diaryl diketones have been reported, involving the oxidation of α-halo and α-hydroxyl ketones, − alkene and alkyne oxidation, − oxidative cleavage of 1,3-diketones, − benzyl phenyl ketone oxidation, − oxidative decarboxylative coupling of arylpropiolic/cinnamic acids with arylboronic acids or aryl halides, − and oxidative rearrangement of α,β-unsaturated diaryl ketones . Among the above methods, the direct oxidation of benzyl phenyl ketone has emerged as a powerfully straightforward strategy to synthesize 1,2-diaryl diketones.…”