The chemistry of heterocyclic carbenes has experienced a rapid development over the last years. In addition to the imidazolin-2-ylidenes, a large number of cyclic diaminocarbenes with different ring sizes have been described. Aside from diaminocarbenes, P-heterocyclic carbenes, and derivatives with only one, or even no heteroatom within the carbene ring are known. New methods for the synthesis of complexes with N-heterocyclic carbene ligands such as the oxidative addition or the metal atom template controlled cyclization of β-functionalized isocyanides have been developed recently. This review summarizes the new developments regarding the synthesis of N-heterocyclic carbenes and their metal complexes.

Heterocyclic Carbenes: Synthesis and Coordination Chemistry

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.

2.3.5. Multi-NHCs Linked by Spacers 3568 2.4. The Ag2O Route 3570 2.4.1. Feasibility 3570 2.4.2. Complications 3571 2.4.3. Theoretical Consideration 3572 2.5. Applications 3572 2.5.1. Ag(I)-NHCs in NHC Transfer 3572 2.5.2. Ag(I)-NHCs in Catalysis 3572 2.5.3. Ag(I)-NHCs in Medicine 3572 2.5.4. Ag(I)-NHCs in Nanomaterials 3573 3. Au(I)and Au(III)-NHCs 3573 3.1. Historical Background 3573 3.2. General Synthetic Methods 3573 3.3. Formation of Au(I)and Au(III)-NHCs 3574 3.3.1. Neutral [Au(NHC)L] 3574 3.3.2. Ionic [Au(NHC)L][Anion] 3576 3.3.3. Multinuclear Au(I)-NHCs 3578 3.3.4. Other Classes of Au(I)-NHCs 3578 3.3.5. Au(III)-NHC Complexes 3579 3.4. Applications 3579 3.4.1. Au(I)and Au(III)-NHCs in Catalysis 3579 3.4.2. Au(I)-NHCs in Medicine 3580 4. Cu(I)and Cu(II)-NHCs 3581 4.1. Historical Background 3581 4.2. General Synthetic Methods 3582 4.3. Formation of Cu(I)and Cu(II)-NHCs 3583 4.3.1. Complexes Containing the Cu(NHC)2 Core 3583 4.3.2. [Cu(NHC)(Halide)] 3583 4.3.3. [Cu(NHC)(Ligand)] 3584 4.3.4. Multinuclear Cu(I)and Cu(II)-NHCs 3589 4.4. Catalysis 3591 4.4.1. Past Events 3591 4.4.2. Recent Advancements 3591 5. Photoluminescence 3592 6. Conclusions 3594 7. Abbreviations 3594 8. Acknowledgments 3595 9. References 3595

Coinage Metal−N-Heterocyclic Carbene Complexes

Palladium-catalyzed cross-coupling reactions enable organic chemists to form C-C bonds in targeted positions and under mild conditions. Although phosphine ligands have been intensively researched, in the search for even better cross-coupling catalysts attention has recently turned to the use of N-heterocyclic carbene (NHC) ligands, which form a strong bond to the palladium center. PEPPSI (pyridine-enhanced precatalyst preparation, stabilization, and initiation) palladium precatalysts with bulky NHC ligands have established themselves as successful alternatives to palladium phosphine complexes. This Review shows the success of these species in Suzuki-Miyaura, Negishi, and Stille-Migita cross-couplings as well as in amination and sulfination reactions.

The development of bulky palladium NHC complexes for the most-challenging cross-coupling reactions.

An air-stable and highly efficient PdCl2–Dppc+ PF6−–[bmim][PF6] catalytic system has been developed for the Suzuki coupling reaction of various aryl bromides with phenylboronic acid. The catalytic system can be recycled at least 10 times with minimal loss of activity. Copyright © 2006 John Wiley & Sons, Ltd.

New recyclable catalytic system: PdCl2-Dppc+ PF6--[bmim][PF6] for the Suzuki coupling reaction

An air-stable, copper-free and highly efficient Dppc+PF6−–PdCl2–[bmim][PF6] catalytic system has been developed for the Sonogashira coupling reaction of aryl iodides with various aryl- and alkylacetylenes. The catalytic system allows for facile separation and can be recycled at least eight times with minimal loss of activity. Copyright © 2007 John Wiley & Sons, Ltd.

Dppc+PF6−–PdCl2–[bmim][PF6]–a copper‐free recyclable catalytic system for Sonogashira coupling reaction

Synthesis and application of novel ionic phosphine ligands with a cobaltocenium backbone

In the title cobaltocenium compound, [Co(C5H5)(C17H114P)]PF6, the CoIII atom carries both cyclo­penta­dienenyl and diphenyl­phosphinocyclo­penta­dienyl ligands inclined to each other at 3.2 (1)°. The disordered PF6− anion links with the cobaltocenium cation via weak C—H⋯F hydrogen bonds.

(η5-Cyclopentadienyl)[η5-1-(diphenylphosphino)cyclopentadienyl]cobalt(III) hexafluorophosphate

In the title compound, [Co(C18H27P)]PF6, the P—C(cyclo­penta­dien­yl) bond distance [1.840 (4) A] is significantly shorter than P—C(tert-but­yl) bond distances [1.879 (5) and 1.900 (5) A]. The PF6− anion links to the cobaltocenium cation via weak C—H⋯F hydrogen bonding.

(Di-tert-butyl­phosphino)cobaltocenium hexa­fluoro­phosphate

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New recyclable catalytic system: PdCl2-Dppc+ PF6--[bmim][PF6] for the Suzuki coupling reaction

Dppc+PF6−–PdCl2–[bmim][PF6]–a copper‐free recyclable catalytic system for Sonogashira coupling reaction

Synthesis and application of novel ionic phosphine ligands with a cobaltocenium backbone

(η5-Cyclopentadienyl)[η5-1-(diphenylphosphino)cyclopentadienyl]cobalt(III) hexafluorophosphate

(Di-tert-butylphosphino)cobaltocenium hexafluorophosphate

Yong Ren

Author Tools

Chat about Author

Papers

New recyclable catalytic system: PdCl2-Dppc+ PF6--[bmim][PF6] for the Suzuki coupling reaction

Dppc+PF6−–PdCl2–[bmim][PF6]–a copper‐free recyclable catalytic system for Sonogashira coupling reaction

Synthesis and application of novel ionic phosphine ligands with a cobaltocenium backbone

(η5-Cyclopentadienyl)[η5-1-(diphenylphosphino)cyclopentadienyl]cobalt(III) hexafluorophosphate

(Di-tert-butyl­phosphino)cobaltocenium hexa­fluoro­phosphate

(Di-tert-butylphosphino)cobaltocenium hexafluorophosphate