Contents to Volume 2. Contents to Volume 1

Transcription

1 to Volume 2 to Volume 1 X 7 Transition Metal-Catalyzed Desulfitative Coupling of Thioorganic Compounds with Boronic Acids 363 Ethel C. Garnier-Amblard and Lanny S. Liebeskind 7.1 General Introduction Boronic Acid-Thioorganic C-S Desulfitative Cross-Couplings Using Catalytic Nickel or Palladium Sulfones as Substrates Sulfonyl Chlorides as Reaction Partners Sulfonium Salts as Substrates Thiol Esters as Substrates Thioethers and Related Substrates Thioamides and Thioureas as Substrates Applications in Organic Synthesis Functionalization of Heteroaromatic Rings Orthogonal Chemistry Solid-Phase Synthesis A Biologically Relevant Molecules Mechanistic Considerations: Pd-Catalyzed, Cu-Mediated Desulfitative Couplings Thioorganic C-S Desulfitative Cross-Couplings Using Only Catalytic Copper Desulfitative Thiol Ester-Boronic Acid Cross-Couplings under Aerobic Conditions Catalyzed by Cu Only Application in Organic Synthesis: Peptidyl Ketones Mechanistic Considerations Cu-Catalyzed Cross-Couplings under Anaerobic Conditions Mechanistic Considerations Miscellaneous Conclusions 388 References 388 Bibliografische Informationen digitalisiert durch

2 VI 8 Catalytic Additions of Allylic Boronates to Carbonyl and Imine Derivatives 393 Tim C. Elford and Dennis C. Hall 8.1 Introduction Additions to Aldehydes Lewis Acid Catalysis Discovery of Catalytic Allylborations Mechanistic Studies Chiral Lewis Acids Further Developments Lewis Acid-Catalyzed Additions with Chiral Allylboronates B-Chiral Allylic Boronates C-Chiral Allylic Boronates Bronsted Acid Catalysis Discovery of Protic Acid Catalyzed Allylborations Mechanistic Studies Further Advances Chiral Bransted Acid Catalysis Discovery and Optimization Further Catalyst Development and Mechanistic Studies Additions to Ketones Introduction Catalytic Methods Utilizing Metal-Based Catalysts Catalytic Methods Utilizing Diol-Based Catalysts Additions to Imine Derivatives Introduction Catalytic Methods Utilizing Metal-Based Catalysts Catalytic Methods Utilizing Diol-Based Catalysts Conclusions 422 References Recent Advances in Nucleophilic Addition Reactions of Organoboronic Acids and Their Derivatives to Unsaturated C-N Functionalities 427 Timothy R. Ramadhar and Robert A. Batey 9.1 Introduction Recent Advances in the Petasis Borono-Mannich Reaction Advances in Synthetic Methods Microwave Accelerated Reactions Solvents and Additives Catalytic Enantioselective Reactions Substrate Scope Applications in Combinatorial and Solid-Phase Synthesis Application toward the Synthesis of Natural Products and Pharmacological Agents Computational Analysis 442

3 VII Petasis Reaction Variants Reactions of N-Acyliminium Ions with Organoboronic Acids and Their Derivatives Advances in Metal-Catalyzed Additions with Organoboronic Acids and Their Derivatives Rhodium-Catalyzed Additions Arylation of Imines Diastereoselective Arylation and Alkenylation of Chiral N-Sulfinylimines Enantioselective Arylation of Imines Arylation of Nitriles and Cyanoformates Arylation and Alkenylations of Isocyanates Palladium-Catalyzed Additions Arylation of Imines Diastereoselective Arylation of Chiral N-Sulfinylimines Enantioselective Arylation of Imines Arylation of Nitriles Arylation of Isocyanates Copper-Catalyzed Oxidative Addition Metal-Catalyzed Boration Metal-Catalyzed Domino Transformations Addition Reactions Involving Imines Addition Reactions Involving Nitriles Addition Reactions Involving Isocyanates Conclusions 472 References Asymmetric Homologation of Boronic Esters with Lithiated Carbamates, Epoxides, and Aziridines 479 Matthew P. Webster and Varinder K. Agganval 10.1 Introduction Lithiated Primary Alkyl Carbamates for the Homologation of Boranes and Boronic Esters Synthesis and Reaction of a-carbamoyloxy-alkylboronates Direct Homologation of Boranes and Boronic Esters Synthesis and Application of Allylboron Reagents Lithiated Secondary Carbamates for the Homologation of Boranes and Boronic Esters Benzylic N-Iinked Lithiated Carbamates for the Homologation oftrialkylboranes Lithiated Epoxides for the Homologation of Boronic Esters Lithiated Aziridines for the Homologation of Boronic Esters Conclusions 501 References 502

4 VIII 11 Organotrifluoroborates: Organoboron Reagents for the Twenty-First Century 507 Cary A. Molander and Ludivine Jean-Gérard 11.1 Introduction Synthetic Approaches to Organotrifluoroborates Elaboration of Organotrifluoroborates via Transformations of Pendant Functional Groups Substitution Reactions Oxidation Reactions Catalytic Hydrogénation Reactions Reductive Animation Reactions Wittig and Horner-Wadsworth-Emmons Reactions TosMIC Condensation Reactions Huisgen Dipolar Cycloadditions Metal-Halogen Exchange and Cross-Coupling Hydroboration Reactions: Generation of Dibora Species and Selective Cross-Coupling Diels-Alder Reactions Transition Metal-Catalyzed Processes Cross-Coupling Reactions Cross-Coupling of Potassium Aryl- and Heteroaryltrifluoroborates Cross-Coupling of Potassium Alkenyltrifluoroborates Cross-Coupling of Potassium Alkynyltrifluoroborates Cross-Coupling of Potassium Alkyltrifluoroborates ,2-Addition Reactions ,4-Addition Reactions 535 U.4A C-H Activation Miscellaneous Reactions of Organotrifluoroborates Hydrolysis and Related Reactions Animation and Amidation Reactions Halogenation Reactions Carbon-Carbon Bond-Forming Reactions with Activated Electrophiles Reactions with Oxocarbenium Ions Mannich and Related Reactions Conclusions 546 References Borate and Boronic Acid Derivatives as Catalysts in Organic Synthesis 551 Joshua N. Payette and Hisashi Yamamoto 12.1 Introduction Nonchiral Boron-Based Catalysis Amide Condensation Esterification Reactions Aldol and Biginelli Reactions 560

5 IX 12.3 Chiral Boron-Based Catalysis VAPOL/VANOL + B(OPh) 3 Catalysts Aziridination Reactions Hetero Diels-Alder Reaction Cationic Oxazaborolidine Catalysts Cycloaddition Reactions Cyanosilylation Reactions Mukaiyama-Michael Reactions ß-Lactone Synthesis Oxazaborolidinone Catalysts Mukaiyama-Michael Reactions Mukaiyama Aldol Reactions Diels-Alder Reactions Oxazaborolidinone/Substrate Complexation Studies Spiroborate Catalysts ,2-Reduction of Prochiral Ketones ,2 Reduction of ( )-Benzyl Oxime Ethers Bisoxazaborolidinone: A Novel Bis-Lewis Acid Tartaric Acid-Derived Boronate Ester for 1,2 and 1,4 Reductions of Carbonyl Compounds Conclusion 587 References Applications of Boronic Acids in Chemical Biology and Medicinal Chemistry 591 Nanting Ni and Binghe Wang 13.1 Introduction Boronic Acids as Potential Medicinal Agents Bacterial Quorum Sensing Inhibitors Antimicrobial and Antifungal Agents The Story of Bortezomib: New Insights Probes for Detecting Reactive Oxygen Species MRI and PET Agents for in vivo Carbohydrate Imaging Carbohydrate Biomarker Binding Agents and Sensors Cell Surface Carbohydrate Binders Aptamers for Glycoproteins Genetically Encoded Boron-Containing Amino Acid Cell Permeable Sensors for the Tetraserine Motif Application of Boronic Acids in Synthesis Chemistry Conclusions 617 References Boronic Acids in Materials Chemistry 622 Jie Liu and John J. Lavigne 14.1 Introduction Linear Boronate-Iinked Materials 624

6 X Covalently Bonded Boronate Assemblies Supramolecular Boronate Assemblies Side-Chain-Functionalized Boronate Materials Macrocydes and Cages Covalent Bonding Boronate Assemblies Supramolecular Boronate Assemblies Complex Hybrid Structures Networks Covalent Bonding Boronate Assemblies Supramolecular Boronate Assemblies Summary and Outlook 671 References 673 Index 677 to Volume 1 Foreword V Preface XV List of Contributors XIX 1 Structure, Properties, and Preparation of Boronic Acid Derivatives: Overview of Their Reactions and Applications 2 Dennis G. Hall 2 Metal-Catalyzed Borylation of C-H and C-Halogen Bonds of Alkanes, Alkenes, and Arènes for the Synthesis of Boronic Esters 235 Tatsuo Ishiyama and Norio Miyaura 3 Transition Metal-Catalyzed Element-Boryl Additions to Unsaturated Organic Compounds 271 Michinori Suginome and Toshimichi Ohmura 4 The Contemporary Suzuki-Miyaura Reaction 223 Cory Valente and Michael G. Organ 5 Rhodium- and Palladium-Catalyzed Asymmetric Conjugate Additions of Organoboronic Acids 263 Guillaume Berthon-Gelloz and Tamio Hayashi 6 Recent Advances in Chan-Lam Coupling Reaction: Copper-Promoted C-Heteroatom Bond Cross-Coupling Reactions with Boronic Acids and Derivatives 315 Jennifer X. Qiao and Patrick Y.S. Lam