Carbonyl compounds have attracted considerable attention due to their extensive applications in drug discovery. Furthermore, they are important synthetic intermediates for the construction of carbon‐carbon and carbon‐heteroatom bonds. Transition‐metal‐catalyzed carbonylation via the insertion of CO is one of the most efficient and straightforward strategies to access carbonyl compounds. However, most of the transition‐metal‐catalyzed carbonylative reactions require expensive and toxic noble‐metal catalysts. Therefore, there is a growing demand for the exploration of nickel‐catalyzed carbonylative reactions via the insertion of CO due to the earth abundance and low cost of nickel. Compared with the well‐established palladium‐catalyzed carbonylative reactions, nickel‐catalyzed analogous transformations have been relatively underdeveloped. This is primarily because CO strongly binds to nickel, often resulting in catalyst poisoning. In recent years, some research groups have focused on using CO surrogates or NN2 pincer nickel catalyst to circumvent the formation of Ni(CO)4. Nickel‐catalyzed carbonylation has been applied in the construction of carbonyl‐containing compounds, such as ketones, carboxylic acids, thioesters, acyl chloride and carboxamides.This article is protected by copyright. All rights reserved.

Recent advances in nickel catalyzed carbonylative reactions via the insertion of Carbon Monoxide

A visible-light-mediated sustainable approach for metal-free oxygenation of quinoxalin-2(1H)-one by employing Mes-Acr-MeClO4 as a photocatalyst without using any additive or cocatalyst is reported here. O2 served as the eco-friendly and green oxidant source for this conversion. In addition, the protocol exhibited high regioselectivity and tolerance toward a broad spectrum of functional groups to furnish quinoxaline-2,3-diones in good to excellent yields.

Visible-Light Promoted Regioselective Oxygenation of Quinoxalin-2(1H)-ones Using O2 as an Oxidant.

The electrochemical synthesis of N-aroylsulfoximines features the use of tetra-n-butylammonium iodide (TBAI) as the medium and a broad substrate scope, thus affording a wide range of N-aroylated sulfoximines in moderate to good yields. The advantages of this electrochemical strategy are augmented by mild reaction conditions that are external oxidant-free, ligand-free, and easy to scale up to gram scale. Both the control experiments and the mechanistic studies revealed that the whole electrochemical process proceeded through a palladium (II/IV/II) catalytic cycle.

Electrochemical Oxidative Carbonylation of NH-Sulfoximines.

Benzyne and related arynes are classical high-energy species with a rich history of widespread applications in synthesis. However, despite several synthetic routes being available to generate arynes and their precursors, none represents an ideal entry to benzyne chemistry in view of safety, scalability, and sustainability. Here we report a new photochemical flow process allowing for the generation of benzyne precursors in high yields and throughput, with easy isolation of multigram quantities of products. This process leverages a catalyst-free photochemical rearrangement via a photoexcited nitro arene which involves a cyclic hydroxylamine intermediate that has been fully characterized. The resulting precursors were converted to benzynes via a second photochemical flow process generating heterocyclic targets upon trapping with azide and sydnone partners. Remarkably, when reacting the benzyne precursors with secondary amines, a wide range of aryl triazines is obtained in good yields via a third photo-flow transformation. This represents a modular approach to synthesize these species, that avoids the use of potentially explosive diazonium salts. Ultimately, three photochemical flow processes using a single high-power LED light source (365 nm, adjustable in-put power) are presented with manifest benefits compared to batch processing. Moreover, the functionalization of a pendent carboxyl group to form sets of biologically relevant aryl triazine-based amides highlights further applications of these unique and industrially relevant triazine entities. 

Modular Photochemical Flow Synthesis of Structurally Diverse Benzyne and Triazine Precursors

An electrochemical method for thioetherification of NH-sulfoximines with disulfides is reported. The utilization of electrochemistry for facilitating these reactions eliminates the necessity for external oxidants, bases, and metal catalysts.

Electrochemical oxidative cross coupling of NH-sulfoximines with disulfides

Sulfoximines are commonly found in pharmaceuticals, agrochemicals and other biologically active compounds. However, limited reports exist for their selective functionalization via green and efficient protocols. Herein, we describe an electrochemical...

Electrochemical N-Acylation and N-α-Ketoacylation of Sulfoximines via the Selective Decarboxylation and Dehydration of α-Ketoacids

Photo‐Driven Direct C–H Arylation of Quinoxalin‐2(1H)‐ones with Aryltriazenes under Catalyst‐Free and Ambient Conditions

Copper-Catalyzed Divergent C-H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines.

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