Transition metal-mediated formation of C-N bonds is an essential synthetic methodology. The discovery of the Chan-Lam amination provided a C-N bond forming process that was mild, convenient, and inexpensive, offering an alternative to complementary methods using other transition metals (TMs). Over the past 20 years, this reaction has seen considerable development in its scope of application, uptake into industry, and understanding of its mechanism. This review provides an account of the development of the Chan-Lam amination, highlighting progress and notable examples of application since 2011. Focus is given to evolution in mechanistic understanding and selected applications of the methodology within medicinal and process chemistry.

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Mechanistic Development and Recent Applications of the Chan-Lam Amination.

Over the course of the past 15 years the success story of N-heterocyclic carbene (NHC) compounds in organic, inorganic, and organometallic chemistry has been extended to another dimension. The immobilization of NHC compounds, undergoing continuous diversification, broadens their range of applications and leads to new solutions for challenges in catalytic and synthetic chemistry. This review intends to present a synthetic toolkit for the immobilization of NHC compounds, giving the reader an overview on synthetic techniques and strategies available in the literature. By individually summarizing and assessing the synthetic steps of the immobilization process, a comprehensive picture of the strategies and methodologies for the immobilization of NHC compounds is presented. Furthermore, the characterization of supported NHC compounds is discussed in detail in order to set up necessary criteria for an in-depth analysis of the immobilized derivatives. Finally, the catalytic applications of immobilized NHC compoun...

Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective.

N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple aromatic halides by simple amines works with many of the described methods in high yield, the reactions may require detailed optimization if applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three main N-arylation methods in their application to the synthesis of biologically active compounds: Palladium-catalysed Buchwald–Hartwig-type reactions, copper-mediated Ullmann-type and Chan–Lam-type N-arylation reactions. The discussed examples show that palladium-catalysed reactions are favoured for large-scale applications and tolerate sterically demanding substituents on the coupling partners better than Chan–Lam reactions. Chan–Lam N-arylations are particularly mild and do not require additional ligands, which facilitates the work-up. However, reaction times can be very long. Ullmann- and Buchwald–Hartwig-type methods have been used in intramolecular reactions, giving access to complex ring structures. All three N-arylation methods have specific advantages and disadvantages that should be considered when selecting the reaction conditions for a desired C–N bond formation in the course of a total synthesis or drug synthesis.

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-7-10.pdf

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds

In recent years, palladium-catalyzed direct arylation of (hetero)aromatics with aryl halides via a C–H bond activation has become a popular method for generating carbon–carbon bonds; however, such couplings still suffer from several limitations due to the limited functional group tolerance, the lack of regioselectivity of some of these couplings, or the poor reactivity of some substrates. For example, the presence of several halide functional groups on arenes is often not tolerated. In recent years, several new alternative coupling partners have been successfully employed for such couplings, such as RSO2R′ derivatives using Pd or Ru catalysts to afford, after a desulfitative coupling, a variety of biaryls or alkylated arenes which in several cases cannot be obtained using aryl or alkyl halides as the coupling partners. This methodology allows the synthesis of complex molecules in only a few steps and will certainly give simpler access to a very wide variety of new biaryls or alkylated arenes useful to mat...

Functionalization of C–H Bonds via Metal-Catalyzed Desulfitative Coupling: An Alternative Tool for Access to Aryl- or Alkyl-Substituted (Hetero)arenes

Chemoselective acidic hydrolysis of sulfonamides with trifluoromethanesulfonic acid has been evaluated as a deprotection method and further extended to more complex synthetic applications. In contrast to conventional troublesome sulfonamide hydrolysis, a near-stoichiometric amount of acid was found to be sufficient to bring about efficient deprotection of various neutral or electron-deficient N-arylsulfonamides, whereas electron-rich substrates provided sulfonyl group migration products. The deprotection method developed is fully selective for N-arylsulfonamides, and the possibility to discriminate among various different sulfonamides is demonstrated.

Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications.

A simple copper salt catalyzed N-arylation reaction with arylboronic acids is reported. In the presence of a catalytic amount of a simple copper salt, the coupling of arylboronic acids with imides was performed in MeOH to give N-arylimides in excellent yields: a variety of amines, amides and sulfonamides could also be successfully coupled with arylboronic acids to give cot-responding N-arylated products in moderate yields.

A simple copper salt catalyzed N-arylation of amines, amides, imides, and sulfonamides with arylboronic acids

An effective and easy-to-handle process for the desulfitative Suzuki cross-couplings of arylsulfonyl chlorides and boronic acids in the presence of a recyclable polymer-supported NHC-Pd complex was developed. The supported catalyst could be reused several times with little loss of catalytic activity.

Desulfitative Suzuki Cross-Couplings of Arylsulfonyl Chlorides and Boronic Acids Catalyzed by a Recyclable Polymer-Supported N-Heterocyclic Carbene-Palladium Complex Catalyst

A Simple Copper Salt Catalyzed N‐Arylation of Amines, Amides, Imides, and Sulfonamides with Arylboronic Acids.

Desulfitative Suzuki Cross‐Coupling of Arylsulfonyl Chlorides and Boronic Acids Catalyzed by a Recyclable Polymer‐Supported N‐Heterocyclic Carbene—Palladium Complex Catalyst.

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A simple copper salt catalyzed N-arylation of amines, amides, imides, and sulfonamides with arylboronic acids

Desulfitative Suzuki Cross-Couplings of Arylsulfonyl Chlorides and Boronic Acids Catalyzed by a Recyclable Polymer-Supported N-Heterocyclic Carbene-Palladium Complex Catalyst

A Simple Copper Salt Catalyzed N‐Arylation of Amines, Amides, Imides, and Sulfonamides with Arylboronic Acids.

Desulfitative Suzuki Cross‐Coupling of Arylsulfonyl Chlorides and Boronic Acids Catalyzed by a Recyclable Polymer‐Supported N‐Heterocyclic Carbene—Palladium Complex Catalyst.