Zinc Catalysis: Applications in Organic Synthesis (eBook)

Stephan Enthaler is the leader of a young researcher's group in the field of homogeneous catalysis at the Technical University Berlin, Germany. He studied chemistry at the University of Rostock (Germany) and obtained his PhD from the Leibniz-Institute for Catalysis at the University of Rostock under the supervision of Prof. M. Beller. Afterwards he moved to Massachusetts Institute of Technology (MIT, Cambridge, USA) for postdoctoral studies. In 2009, he returned to Germany to the Technical University Berlin to work within the Cluster of Excellence "Unifying Concepts in Catalysis" (UniCat). His research interests are focused on the development of homogeneous catalysts for organic transformations and for chemical recycling of polymers. Xiao-Feng Wu leads a junior research group at Zhejiang Sci-Tech University (China) and Leibniz-Institute for Catalysis in Rostock (Germany). He studied chemistry at Zhejiang Sci-Tech University, where he obtained his bachelor's degree in science in 2007. In the same year, he went to Université de Rennes 1 (France) to work with Prof. C. Darcel. He obtained his master's degree there in 2009 and then joined the group of Prof. M. Beller at the Leibniz-Institute for Catalysis in Rostock, where he completed his PhD thesis in 2012. His research interests include carbonylation reactions, heterocycle synthesis, and the catalytic application of cheap metals.

INTRODUCTION: ZINC CATALYSTS FOR ORGANIC TRANSFORMATIONS

ZINC-CATALYZED REDUCTIONS OF UNSATURATED COMPOUNDS
Introduction
Hydrosilylation of Unsaturated Compounds
Hydrogenation
Transfer Hydrogenation of Unsaturated Compounds
Concluding Remarks

ZINC-CATALYZED OXIDATION REACTIONS
Introduction
Oxidative Transformation of Alkenes
Oxidative Transformation of Aldehydes
Oxidative Transformation of C?X Bonds (X=O, N, and S)
Oxidative Functionalization of sp3 C?H Bonds
Other Oxidative Reactions with Redox-Active Ligands
Summary and Outlook

ZINC-CATALYZED FRIEDEL-CRAFTS REACTIONS
Introduction
Friedel-Crafts Acylation
Friedel-Crafts Alkylations
Conclusions

ZINC-CATALYZED HYDROAMINATION REACTIOS
Introduction
Inorganic Zinc Salts as Catalysts
Aminotroponiminate Zinc Complexes as Catalysts
Other Zinc Organometallic Compounds as Catalysts
Double Metal Cyanide Catalysts
Summary

ZINC-CATALYZED C-C BOND FORMATION
Introduction
Zinc-Catalyzed Aldol-Type Reactions
Zinc-Catalyzed Cycloaddition Reactions
Zinc-Catalyzed Addition of Organometallic Reagents to Carbonyl and Related Compounds
Zinc-Catalyzed Cross-Coupling Reactions
Radical Reactions Involving Catalytic Amounts of Zinc
Zinc-Catalyzed Reactions through Alkyne Activation
Zinc-Catalyzed Cyclopropanation Reactions
Other Zinc-Catalyzed Reactions
Summary and Outlook

ZINC-CATALYZED C-N AND C-O BOND FORMATION REACTIONS
Introduction
Zinc-Catalyzed C-N Bond Formation Reactions
Zinc-Catalyzed C-O Bond Formation Reactions
Summary and Conclusions

ZINC-CATALYZED TRANSFORMATIONS OF CARBON DIOXIDE
Introduction
Zinc Catalysts for the Copolymerization of Epoxides and CO2
Zinc-Catalyzed Synthesis of Cyclic Carbonates Utilizing Carbon Dioxide as a Chemical Feedstock
Summary

ZINC-CATALYZED DEPOLYMERIZATION REACTIONS
Introduction
Zinc-Catalyzed Depolymerization of Polyethers
Zinc-Catalyzed Depolymerization of Polyesters
Zinc-Catalyzed Depolymerization of Silicones
Summary

APPLICATIONS OF ZINC-PROMOTED REACTION IN TOTAL SYNTHESIS
Introduction
Zinc-Promoted Reactions without Ligands
Zinc-Mediated Reactions with Ligands
Other Zinc-Promoted Reactions

APPLICATION OF ORGANOZINC REAGENTS IN OXIDATIVE COUPLING REACTIONS
Introduction
Oxidative Coupling between Zinc Reagents and C(sp) Nucleophiles
Oxidative Coupling between Organozinc Reagents and C(sp2) Nucleophiles
Oxidative Coupling between Organozinc Reagents and C(sp3) Nucleophiles
Oxidative Coupling between Organozinc Reagents and Heteroatom Nucleophiles
Conclusion

Index