C-C Cross Couplings with 3d Base Metal Catalysts

Description

This volume presents recent progress on 3d base metal catalyzed C-C cross coupling reactions. The contributions provide detailed discussions on the use of cheap metal catalysts such as Cr, Mn, Fe, Co, Ni, Cu, and Zn to construct Csp2-Csp2, Csp2-Csp3 and Csp3-Csp3 bonds with a variety of substrates. These non-noble metal catalyst have many advantages such as being inexpensive, having low toxicity and are environmentally benign. Therefore the use of cheap metal catalysts in organic synthesis has gained much attention in efforts to develop more sustainable synthetic green chemistry. Each chapter is written by international experts in the field and is a great resource for students, researchers and chemists working in industry to gain an overview on the latest developments. Cover Topics in Organometallic Chemistry Series № 93 C-C Cross Couplings with 3d Base Metal Catalysts Copyright Preface Contents C-C Cross Couplings with Chromium Catalysis Contents 1. Introduction 2. Cr-Catalyzed Cross Couplings of C-O Bonds to Form C-C Bonds 2.1 Cr-Catalyzed Kumada Coupling of C-O Bonds 2.2 Cr-Catalyzed Cross-Electrophile-Coupling of C-O Bonds 3. Cr-Catalyzed Cross Couplings of C-N Bonds to Form C-C Bonds 3.1 Cr-Catalyzed Kumada Coupling of C-N Bonds 3.2 Cr-Catalyzed Cross-Electrophile-Coupling of C-N Bonds 4. Cr-Catalyzed Cross Couplings of C-Halide, C-S and C-P Bonds to Form C-C Bonds 5. Conclusions References Mn-Catalyzed C-C Coupling Reactions Contents 1. Introduction 2. C-H Activation 2.1 Addition to Polar Bonds 2.2 Addition to Nonpolar Bonds 2.3 Addition to Mn=C Bond 2.4 Substitutive C-H Activation 3. Hydrocarbofunctionalization of Unsaturated C-C Bond Without C-H Activation 4. Conclusion References Iron-Catalyzed Carbon-Carbon Coupling Reaction Contents 1. Introduction 2. Fe-Catalyzed Coupling Reaction of Electrophilic Reagents and Nucleophilic Reagents 2.1 Fe-Catalyzed C(sp2)C(sp3) Coupling Reaction 2.1.1 Fe-Catalyzed C(sp2)X-C(sp3)M Coupling 2.1.2 Fe-Catalyzed C(sp3)X-C(sp2)M Coupling 2.2 Fe-Catalyzed C(sp2)-C(sp2) Coupling 2.3 Fe-Catalyzed C(sp3)-C(sp3) Coupling 2.4 Fe-Catalyzed C(sp3)-C(sp) Coupling 3. Fe-Catalyzed C-H Direct Coupling 3.1 Fe-Catalyzed C-H Direct Coupling-C(sp3)-C(sp2) Coupling 3.2 Fe-Catalyzed C-H Direct Coupling-C(sp2)-C(sp2) Coupling 3.3 Fe-Catalyzed C-H Direct Coupling-C(sp2)-C(sp) Coupling 4. Fe-Catalyzed Oxidative/Reductive Coupling 4.1 Fe-Catalyzed Oxidative Coupling 4.2 Fe-Catalyzed Reductive Coupling 5. Summary and Outlook References Cobalt-Catalyzed C-C Coupling Reactions with Csp3 Electrophiles Contents 1. Introduction 2. Cobalt-Catalyzed C-Csp3 Coupling Reactions Using Organometallic Reagents 2.1 Cobalt-Catalyzed C-Csp3 Coupling Reactions with Organomagnesium Reagents 2.2 Cobalt-Catalyzed C-Csp3 Coupling Reactions with Organozinc Reagents 2.3 Cobalt-Catalyzed C-Csp3 Coupling Reactions with Mn-, Al-, and B-Based Reagents 3. Cobalt-Catalyzed Reductive C-Csp3 Coupling Reactions Between Two Electrophiles 4. Cobalt-Catalyzed C-Csp3 Coupling Reactions via C-H Activations 5. Conclusions References Co-catalyzed C-C Coupling Reactions with Csp2 Electrophiles Contents 1. Introduction 2. Csp2 Electrophile with Grignard Regents 2.1 Csp2-Csp2 Bonds Formation 2.2 Csp2-Csp3 Bonds Formation 3. Csp2 Electrophile with Organozinc Reagents 3.1 Csp2-Csp3 Bonds Formation 3.2 Csp2-Csp Bonds Formation 4. Csp2 Electrophile with Other Organometallic Reagents 5. Co-catalyzed Reductive Cross-Coupling Involving Csp2 Electrophiles 5.1 Csp2-Csp3 Bonds Formation 5.2 Formation of Csp2-Csp2 Bonds 5.2.1 Formation of Ar-Vinyl Derivatives 5.2.2 Formation of Ar-(Het)Ar Derivatives 6. Conclusion References Recent Advances in Nickel-Catalyzed C-C Cross-Coupling Contents 1. Introduction 2. Classical Cross-Coupling 2.1 Kumada Cross-Coupling 2.1.1 C(sp2)-C(sp2) Bond Formation 2.1.2 C(sp2)-C(sp3) Bond Formation 2.1.3 C(sp3)-C(sp3) Bond Formation 2.2 Negishi Cross-Coupling 2.2.1 C(sp2)-C(sp3) Bond Formation 2.2.2 C(sp3)-C(sp3) Bond Formation 2.3 Suzuki-Miyaura Cross-Coupling 2.3.1 C(sp2)-C(sp2) Bond Formation 2.3.2 C(sp2)-C(sp3) Bond Formation 2.3.3 C(sp3)-C(sp3) Bond Formation 2.4 Stille Cross-Coupling 2.5 Mizoroki-Heck Cross-Coupling 3. Reductive Cross-Coupling 3.1 C(sp2)-C(sp2) Bond Formation 3.2 C(sp2)-C(sp3) Bond Formation 3.3 C(sp3)-C(sp3) Bond Formation 4. Oxidative Cross-Coupling 5. Cross-Coupling of C-H Bonds 5.1 C(sp2)-C(sp2) Bond Formation 5.2 C(sp2)-C(sp3) Bond Formation 5.3 C(sp3)-C(sp3) Bond Formation 6. Conclusion References Copper-Catalyzed C-C Bond Formation via Carboxylation Reactions with CO2 Contents 1. Introduction 2. Copper-Catalyzed Carboxylation of Organometallic Reagents to Form C-C Bonds 2.1 Copper-Catalyzed Carboxylation of Organoboron Reagents 2.2 Copper-Catalyzed Carboxylation of Organosilane Reagents 2.3 Copper-Catalyzed Carboxylation of Organoaluminum Reagents 2.4 Copper-Catalyzed Carboxylation of Organotin Reagents 3. Copper-Catalyzed Carboxylation of Organic Halides to Form C-C Bonds 4. Copper-Catalyzed Carboxylation of C-H Bonds to Form C-C Bonds 5. Copper-Catalyzed Carboxylation of C-C Double Bonds to Form C-C Bonds 5.1 Carboxylation of Alkenes 5.2 Carboxylation of Allenes 5.3 Carboxylation of Dienes 6. Copper-Catalyzed Carboxylation of C-C Triple Bonds to Form C-C Bonds 6.1 Carboxylation of Terminal Alkynes 6.2 Carboxylation of Internal Alkynes 6.3 Carboxylation of Benzynes 7. Conclusion References Cu-Catalyzed C-C Bond Formation with CO Contents 1. Introduction 2. Hydride Nucleophile 3. Boron Nucleophile 4. Carbon (Pro-)Nucleophiles 4.1 Carbonylative Cross Coupling 4.2 Insertion into CuH or CuBpin Intermediates 4.3 Radical Cascade 5. Nitrogen Nucleophiles 6. Oxygen Nucleophiles 7. Silicon Nucleophiles 8. Conclusions References Cu-Catalyzed C-C Coupling Reactions Contents 1. Introduction 2. Breakthrough After Ullmann Coupling Reaction 3. Untapped Potential of Copper Catalysts in the Coupling Reactions 3.1 Coupling with Terminal Alkynes 3.2 Coupling with Grignard Reagents 3.3 Coupling with Organozinc Reagents 3.4 Coupling with Organoboron Reagents 3.5 Coupling with Organotin Reagents 3.6 Coupling with Organosilicon Reagents 3.7 Coupling with Organoindium and Organoaluminium Reagents 3.8 Coupling with Organomanganese Reagents 4. Copper-Catalyzed Cyanations of Aryl Halides 5. Copper-Catalyzed Alkynylation, Alkenylation, and Allylation 5.1 Copper-Catalyzed Alkynylation Reactions of Aryl Compounds 5.1.1 Copper-Catalyzed Preparation of Aryl-Ynes via Stille-Type Cross-Coupling Reactions 5.1.2 Copper-Catalyzed Preparation of Aryl-Ynes via Sonogashira-Type Cross-Coupling Reaction 5.1.3 Synthesis of Aryl-Ynes by Direct C-H 5.2 Copper-Catalyzed Alkenylation of Aryl Derivatives 5.2.1 Copper-Catalyzed Preparation of Aryl-Enes via Stille-Type Cross-Coupling Reaction 5.2.2 Copper-Catalyzed Preparation of Aryl-Enes via Heck-Type Cross-Coupling 5.2.3 Copper-Catalyzed Preparation of Aryl-Enes via Suzuki-Miyaura-Type Cross-Coupling 5.2.4 Copper-Catalyzed Preparation of Aryl-Enes via Direct C-H Activation of Arenes 5.2.5 Copper-Catalyzed Synthesis of Aryl-Enes via Decarboxylative Cross-Coupling 5.3 Copper-Catalyzed Synthesis of Allyl-Aryl Bonds 5.3.1 Copper-Catalyzed Synthesis of Diynes Through Alkylation of Alkyl Derivatives 5.3.2 Copper-Catalyzed Synthesis of Symmetric and Unsymmetric 1,3 Diynes 5.3.3 Copper-Catalyzed Synthesis of 1,4 Diynes 5.3.4 Copper-Catalyzed Synthesis of Dienes via Alkenylation of Alkynyl Derivatives 6. Copper-Catalyzed Oxidative Cross-Coupling Reaction Between Two Nucleophiles for C-C Bond Formation 6.1 Oxidative Cross-Coupling of Aryl Boronic Acids with Hydrocarbons/Nucleophiles 6.2 Copper-Catalyzed Oxidative Decarboxylative Cross-Coupling for C-C Formation 7. Copper-Catalyzed Cross-Dehydrogenative Coupling (CDC) for C-C Bond Formation 7.1 Cross-Dehydrogenative C(sp3)-C(sp) Bond Formation (Alkynylation) 7.2 Cross-Dehydrogenative C(sp3)-C(sp2) Bond Formation (Arylation) 7.3 Cross-Dehydrogenative C(sp3)-C(sp3) Bond Formation (Alkylation) 7.4 Cross-Dehydrogenative C(sp2)-C(sp2) Bond Formation (Aryl-Aryl) 7.5 Cross-Dehydrogenative C(sp)-C(sp) Bond Formation (Diyenes) References Zinc-Catalyzed C-C Coupling Reactions Contents 1. Introduction 2. Sonogashira Reaction 3. Suzuki Type Cross-coupling Reaction 4. Cadiot-Chodkiewicz Reaction 5. Cross-Dehydrogenative Coupling 6. Cross-Coupling Using Organotin Reagent 7. Cross-Coupling Using Grignard Reagent 8. Synthesis of α,β-Acetylenic Ketones 9. Synthesis of Conjugated Dienoate Derivatives 10. Conclusion References