Synthesis of Polysubstituted Furans via Copper-Mediated Annulation of Alkyl Ketones with α,β-Unsaturated Carboxylic Acids

A novel copper-mediated annulation of alkyl ketones with α,β-unsaturated carboxylic acids has been accomplished. This reaction provides a facile and regio-defined method for the synthesis of 2,3,5-trisubstituted furans from simple chemical reagents

Nucleophilic Functionalizations of Aniline Derivatives: Aromatic Pummerer Reaction for Umpolung Halogenation and Hydroxylation on Benzene Ring

In this paper, a metal-free protocol of nucleophilic <i>ortho</i>-halogenation and hydroxylation of anilines via an aromatic Pummerer process is reported

Cu(II)-Promoted Palladium-Catalyzed C–H Ortho-Arylation of <i>N</i>,<i>N</i>‑Dimethylbenzylamines

A novel protocol for palladium-catalyzed arylation of the C­(sp²)–H bond directed by a <i>N</i>,<i>N</i>-dimethylaminomethyl group in the presence of AgOAc and Cu­(OAc)₂·H₂O is described. Various aryl iodides proved to be efficient coupling partners, furnishing the corresponding ortho monoarylated or diarylated arenes in moderate to good yields. Cu­(OAc)₂·H₂O is found to be the important additive to improve the yields in this transformation

Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups

A novel palladium-catalyzed <i>ortho</i>-C­(sp²)–H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the <i>ortho</i> olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities

Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups

A novel palladium-catalyzed <i>ortho</i>-C­(sp²)–H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the <i>ortho</i> olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities

Palladium-Catalyzed Oxidative Acetoxylation of Benzylic C–H Bond Using Bidentate Auxiliary

Pd­(OAc)₂-catalyzed oxidative acetoxylation of benzylic C–H bonds utilizing a bidentate system has been explored. A variety of picolinoyl- or quinoline-2-carbonyl-protected toluidine derivatives react with PhI­(OAc)₂ in the presence of Pd­(OAc)₂ to afford the acetoxylated products in synthetically useful yields. A broad of functionalities, such as CH₃, F, Cl, Br, I, COCH₃, CO₂Et, SO₂CH₃, and NO₂, were tolerated. This transformation provides easy access to 2-hydroxymethylaniline derivatives

Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups

A novel palladium-catalyzed <i>ortho</i>-C­(sp²)–H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the <i>ortho</i> olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities

Direct <i>ortho</i>-Thiolation of Arenes and Alkenes by Nickel Catalysis

The direct thiolation of arenes and alkenes with diaryl disulfides was developed by nickel catalysis. The reaction displayed exceptional compatibility with a wide range of functional groups to regioselectively give the diaryl sulfides and alkenyl sulfides in high yields

Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups

A novel palladium-catalyzed <i>ortho</i>-C­(sp²)–H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the <i>ortho</i> olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities

Modular Synthesis of Tetrasubstituted Pyrroles via an Annulative Migration Reaction of Allenyl Ketones and <i>p</i>‑Toluenesulfonylmethyl Isocyanide

The metal-free cyclization of allenyl ketones and p-toluenesulfonylmethyl isocyanide (TosMIC), promoted by Cs2CO3, provides a convenient access to tetrasubstituted pyrroles in which an acyl group undergoes 1,2-migration. This tandem Michael addition/annulative migration synthetic strategy is general and high-yielding for various substituted allenyl ketones. Moreover, a phosphoryl or ester moiety is also a suitable functionality to enable such migration