Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

A visible light-induced Co-catalyzed highly regio- and stereoselective reductive coupling of vinyl azaarenes and alkynes has been developed. Notably, Hünig's base together with simple ethanol has been successfully applied as the hydrogen sources instead of commonly used Hantzsch esters in this catalytic photoredox reaction. This approach has considerable advantages for the straightforward synthesis of stereodefined multiple substituted alkenes bearing an azaarene motif, such as excellent regioselectivity (>20:1 for >30 examples) and stereoselectivity (>20:1 E / Z ), broad substrate scope and good functional group compatibility under mild reaction conditions, which has been utilized in the concise synthesis of natural product monomorine I. A reasonable catalytic reaction pathway involving protolysis of the cobaltacyclopentene intermediate has been proposed based on the mechanistic studies.

Selective Reductive Coupling of Vinyl Azaarenes and Alkynes via Photoredox Cobalt Dual Catalysis.

Totally different functionalization and construction as two fundamental synthetic protocols have long been applied to furnish azaarene variants. Here, a novel radical-based functionalization-oriented construction strategy by exploiting the electronic properties of azaarenes and the high reactivity of radicals is developed. Under a photoredox catalysis platform, the robust ability of such an artful combination of functionalization with construction is disclosed in the synthesis of valuable 3-azaarene-substituted densely functionalized pyrroles. In addition to the ability to use the readily accessible feedstocks, the high synthetic efficiency and the good functional group tolerance, the substrate scope is broad (81 examples) resulting from the capability to flexibly replace the types of azaarenes and other substituents. Control experiments and density functional theory (DFT) calculations elucidate the plausible mechanism involving the reaction pathways and the important role of NaH2PO4 as an additive in the reaction.

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Radical-based functionalization-oriented construction: rapid assembly of azaarene-substituted highly functionalized pyrroles

C–N cross-coupling bond formation reactions have become valuable approaches to synthesizing anilines and their derivatives, known as important chemical compounds. Recent developments in this field have focused on versatile catalysts, simple operation methods, and green reaction conditions. This review article presents an overview of C–N cross-coupling reactions in pharmaceutical compound synthesis reports. Selected examples of N-arylation reactions of various nitrogen-based compounds and aryl halides are defined for preparing pharmaceutical molecules.

/pdf/applications-of-palladium-catalyzed-c-n-cross-coupling-26fhr4el.pdf

Applications of palladium-catalyzed C–N cross-coupling reactions in pharmaceutical compounds

The present invention relates to injecting a high specificity cytokine antagonist into a diseased intervertebral disc.

Transdiscal administration of specific inhibitors of pro-inflammatory cytokines

Inhibitors of unactivated p38 MAP kinase.

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Inhibitors of unactivated p38 MAP kinase.