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

The coupling of aryl or vinyl halides with terminal acetylenes catalysed by palladium and other transition metals, commonly termed as Sonogashira cross-coupling reaction, is one of the most important and widely used sp2–sp carbon–carbon bond formation reactions in organic synthesis, frequently employed in the synthesis of natural products, biologically active molecules, heterocycles, molecular electronics, dendrimers and conjugated polymers or nanostructures. This critical review focuses on developments in the Sonogashira reaction achieved in recent years concerning catalysts, reaction conditions and substrates (352 references).

Recent advances in Sonogashira reactions

5.4. Miscellaneous Examples 2295 5.4.1. Couplings with Other Catalysts 2295 5.4.2. The Use of Other Boron Reagents 2295 5.4.3. Related Coupling Reactions 2296 5.5. Summary 2297 6. Sonogashira Coupling 2297 6.1. Couplings with Pd Particles 2297 6.2. Studies with Immobilized Palladium Complexes 2299 6.3. Miscellaneous Examples 2301 6.4. Carbonylative Sonogashira Couplings 2302 6.5. Summary 2302 7. Stille Couplings 2302 7.1. Stille Coupling 2302 7.2. Carbonylative Stille Coupling 2304 7.3. Summary 2304 8. Miscellaneous Cross-Coupling Reactions 2304 9. Allylations 2305 9.1. Tsuji-Trost Allylation 2305 9.2. Allylation of Boron Reagents 2306 10. Homocouplings 2307 10.1. Summary 2308 11. C-C Couplings in Continuous Systems 2308 12. Conclusions and Outlook 2311 Author Information 2314 Biography 2314 References 2314

Efficient, selective, and recyclable palladium catalysts in carbon-carbon coupling reactions.

Palladium-catalyzed carbonylative coupling reactions of aromatic halides and related compounds have undergone a rapid development during recent years. Nowadays, a plethora of palladium catalysts are available for the synthesis of ketones, alkynones, chalcones, etc., which are important intermediates in the manufacture of dyes, pharmaceuticals, agrochemicals, and other industrial products. In this critical review, we summarize the development of these carbonylative transformations with carbon nucleophiles (136 references).

Palladium-catalyzed carbonylative coupling reactions between Ar–X and carbon nucleophiles

/pdf/chemicals-from-alkynes-with-palladium-catalysts-2z3b447mxh.pdf

Chemicals from Alkynes with Palladium Catalysts

A phosphine-free carbonylative cross-coupling reaction of aryl iodides with arylboronic acids catalyzed by immobilization of palladium in MCM-41

Palladium-catalyzed addition of diaryl disulfides and diselenides to terminal alkynes in room temperature ionic liquids

Simple and efficient CuI/PEG-400 system for amination of aryl halides with aqueous ammonia

The first heterogeneous carbonylative Sonogashira coupling reaction of terminal alkynes with aryl iodides under atmospheric pressure of carbon monoxide was achieved in the presence of a catalytic amount of MCM-41-supported bidentate phosphine palladium(0) complex [MCM-41-2P-Pd(0)] in good to high yields. This polymeric palladium catalyst can be reused at least 10 times without any decrease in activity.

The first heterogeneous carbonylative Sonogashira coupling reaction catalyzed by MCM-41-supported bidentate phosphine palladium(0) complex

Palladium-catalyzed cross-coupling reactions of phenyl tributylstannyl selenide with aryl and alkyl halides can proceed smoothly in room temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]), to give the corresponding diorganyl selenides in good to high yields. The coupling reaction run in [bmim][PF6] has the advantages of rate acceleration and increase of yield in contrast to the reaction run in toluene. Our system not only avoids the use of easily volatile toluene as a solvent but also solves the basic problem of palladium catalyst reuse.

Wenyan Hao

Papers

A phosphine-free carbonylative cross-coupling reaction of aryl iodides with arylboronic acids catalyzed by immobilization of palladium in MCM-41

Palladium-catalyzed addition of diaryl disulfides and diselenides to terminal alkynes in room temperature ionic liquids

Simple and efficient CuI/PEG-400 system for amination of aryl halides with aqueous ammonia

The first heterogeneous carbonylative Sonogashira coupling reaction catalyzed by MCM-41-supported bidentate phosphine palladium(0) complex

Palladium-catalyzed cross-coupling of PhSeSnBu3 with aryl and alkyl halides in ionic liquids: a practical synthetic method of diorganyl selenides