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(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

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