1.6 Other Intramolecular Decarboxylative Coupling Reactions Decarboxylative Coupling Reaction of Allyl Carboxylates

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1 Contents Part I New Carbon Carbon Coupling Reactions Based on Decarboxylation 1 Transition Metal-Catalyzed Decarboxylation and Decarboxylative Cross-Couplings Introduction Metal-Catalyzed Decarboxylation Reactions Cu-Catalyzed Protodecarboxylation Ag-Catalyzed Protodecarboxylation Au-Catalyzed Protodecarboxylation Pd-Catalyzed Protodecarboxylation Rh-Catalyzed Protodecarboxylation Decarboxylative C C Cross-Coupling Reactions Cross-Coupling Between C COOH and C X Bonds Decarboxylative Heck Couplings Decarboxylative Cross-Coupling of Activated C H/C COOH Cross-Coupling Between C COOH and C M Bonds Decarboxylative Carbon Heteroatom Cross-Coupling Decarboxylative C N Cross-Coupling Decarboxylative C S Cross-Coupling Decarboxylative C P Cross-Coupling Decarboxylative C-Halide Cross-Coupling Decarboxylative Addition Reactions Additions to Aldehydes and Imines Additions to Alkynes Additions to Nitriles ,4-Additions xiii

2 xiv Contents 1.6 Other Intramolecular Decarboxylative Coupling Reactions Decarboxylative Coupling Reaction of Allyl Carboxylates Intramolecular Decarboxylative Cyclization Application of Decarboxylative Coupling Method in the Synthesis of Important Molecules Conclusions and Perspectives References Palladium-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoester with Aryl and Alkenyl Halides Introduction Results and Discussion Investigation of the Reaction Conditions Exploration of the Substrate Scope Mechanistic Study Conclusion Experimental Section and Compound Data General Information Experimental Procedure Characterization of the Products References Synthesis of Polyfluorobiaryls via Copper-Catalyzed Decarboxylative Couplings of Potassium Polyfluorobenzoates with Aryl Bromides and Iodides Introduction Results and Discussion Investigation of Reaction Condition Exploration of the Substrate Scope Mechanistic Study Conclusion Experimental Section and Compound Data General Information General Procedure Characterization of the Products References Palladium-Catalyzed Decarboxylative Couplings of Potassium Polyfluorobenzoates with Aryl Bromides, Chlorides, and Triflates Introduction Investigation of the Reaction Conditions Exploration of the Substrate Scope Mechanistic Study The Cross-Coupling Controlled by the Ligands

3 Contents xv 4.2 Conclusion Experimental Section and Compound Data General Information General Procedures Characterization of the Products References Construction of C(sp 3 ) C(sp 2 ) Bonds Via Palladium-Catalyzed Decarboxylative Couplings of 2-(2-Azaaryl)Acetate Salts with Aryl Halides Introduction Results and Discussion Investigation of the Reaction Conditions Exploration of the Substrate Scope Mechanistic Study Conclusion Experimental Section and Compound Data General Information General Procedure Characterization of the Products References Synthesis of α-aryl Nitriles and α-aryl Acetate Esters Via Palladium-Catalyzed Decarboxylative Couplings of α-cyano Aliphatic Carboxylate Salts and Malonate Monoester Salts with Aryl Halides Introduction Results and Discussion Investigation of the Reaction Conditions Exploration of the Substrate Scope Application of the Method Extending the Concept of Decarboxylative α-arylation to the Synthesis of α-aryl Acetates Conclusion Experiment Section and Compound Data General Information General Procedures Characterization of the Products References Palladium-Catalyzed Decarboxylative Couplings of Nitrophenyl Acetate Salts and Its Derivatives with Aryl Halides Introduction Results and Discussion Investigation of the Reaction Conditions Exploration of Substrate Scope

4 xvi Contents Application of the Reaction in Synthesis of 4-Aryl Quinolines and Dihydroquinolinones Transformation of -NO 2 by Sandmeyer Reaction Conclusion Experimental Section and Compound Data General Information General Procedures Characterization of the Products References Palladium-Catalyzed Decarboxylative Benzylation of α-cyano Aliphatic Carboxylate Salts with Benzyl Electrophiles Introduction Results and Disscussion Investigation of the Reaction Conditions Study of the Substrate Scope Proposed Reaction Mechanism Conclusion Experimental Section and Compound Data General Information Experimental Procedure Characterization of the Products References Part II New Carbon Carbon Coupling Reactions Based on Iron-Catalyzed C H Activation 9 Recent Developments of Iron-Catalyzed Directed C H Activation/C C Bond Formation Reactions Introduction Iron-Catalyzed Direct Arylation of the C H Bonds with Aryl Halides as the Arylation Reagents Iron-Catalyzed Direct Activation of C H Bond Using Organometallic Reagents References β-arylation of Carboxamides Via Iron-Catalyzed C(sp 3 ) H Bond Activation Introduction Results and Discussion Investigation of the Reaction Conditions Exploration of the Substrate Scope Deuterated Experiments Conclusion

5 Contents xvii 10.4 Experimental Section and Compound Data General Information Investigation of the Key Reaction Parameters Characterization of Compounds Deuterium-Labeling and KIE Experiments References Iron-Catalyzed Directed C(sp 2 ) H Bond Functionalization with Organoboron Compounds Introduction Results and Discussion Investigation of the Reaction Conditions Exploration of the Substrate Scope Mechanistic Study Conclusion Experimental Section and Compound Data General Information Experimental Procedures References

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