Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

3.1.2. From Vinylic Grignard Reagents 1437 3.1.3. From Aryl Halides and Alkenyl Acetates 1438 3.2. Aryl-Aryl Cross-coupling 1438 3.2.1. From Aromatic Organometallic Reagents 1438 3.2.2. From Two Aromatic Halides 1440 4. Csp2-Csp3 Cross-coupling Reactions 1440 4.1. Alkenylation 1440 4.1.1. From Aliphatic Organometallic Reagents 1440 4.1.2. From Aliphatic Halides 1442 4.2. Arylation 1442 4.2.1. From Aliphatic Halides 1442 4.2.2. From Aromatic Halides 1445 4.3. Allylation of Aromatic Organometallics 1446 5. Alkynylation 1446 5.1. Pioneering Works 1446 5.2. Benzylation of Acetylenic Grignard Reagents 1446 5.3. Alkylation of Acetylenic Grignard Reagents 1447 5.4. Alkenylation of Acetylenic Grignard Reagents 1447 6. Csp3-Csp3 Cross-coupling 1448 6.1. Allylation 1448 6.1.1. Allylation of Aliphatic Organozinc Compounds 1448

Cobalt-Catalyzed Cross-Coupling Reactions

Sulfur-containing molecules such as thioethers are commonly found in chemical biology, organic synthesis, and materials chemistry. While many reliable methods have been developed for preparing these compounds, harsh reaction conditions are usually required in the traditional methods. The transition metals have been applied in this field, and the palladium-catalyzed coupling of thiols with aryl halides and pseudo halides is one of the most important methods in the synthesis of thioethers. Other metals have also been used for the same purpose. Here, we summarize recent efforts in metal-catalyzed C-S bond cross-coupling reactions, focusing especially on the coupling of thiols with aryl- and vinyl halides based on different metals.

Transition-metal-catalyzed C-S bond coupling reaction.

CuO nanoparticles have been studied for C−N, C−O, and C−S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.

CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: scope and mechanism.

Efficient CuO‐Nanoparticle‐Catalyzed CS Cross‐Coupling of Thiols with Iodobenzene

Copper-catalyzed synthesis of vinyl sulfides.

We report a method for the synthesis of vinyl sulfides using the soluble copper(I) catalyst [Cu(phen)(PPh3)2]NO3. The desired vinyl sulfides are obtained in good to excellent yields, with retention of stereochemistry. This protocol tolerates a wide variety of functional groups or substrates, is palladium-free, and does not require the use of expensive or air-sensitive additives.

Copper-Catalyzed Synthesis of Vinyl Sulfides.

[reaction: see text] We report a method for the synthesis of vinyl sulfides using the soluble copper(I) catalyst [Cu(phen)(PPh3)2]NO3. The desired vinyl sulfides are obtained in good to excellent yields, with retention of stereochemistry. This protocol tolerates a wide variety of functional groups or substrates, is palladium-free, and does not require the use of expensive or air-sensitive additives.

Michael Q. Doherty

Papers

Copper-catalyzed synthesis of vinyl sulfides.

Copper-Catalyzed Synthesis of Vinyl Sulfides.

Copper-catalyzed synthesis of vinyl sulfides.