Ligand Platforms in Homogenous Catalytic Reactions with Metals

Preface ix

Abbreviation xi

Part I?N-Heterocyclic Carbene Ligands in Transition Metal Catalyzed Hydrogen Transfer and Dehydrogenative Reactions 1

1 Oxidation and Hydrogenation Reactions Catalyzed by Transition Metal Complexes Bearing N-Heterocyclic Carbene Ligands 3

1.1 Introduction, 3

1.2 Oxidation of Alcohols Based on Hydrogen Transfer, 3

1.3 Oxidation of Alcohols Based on Dehydrogenation, 10

1.4 Hydrogenation and Transfer Hydrogenation of Carbon-Heteroatom Unsaturated Bonds, 12

1.5 Other Related Hydrogenative Reactions, 21

References, 25

2 Bond-Forming Reactions Catalyzed by Transition Metal Complexes Bearing N-Heterocyclic Carbene Ligands 27

2.1 Introduction, 27

2.2 Carbon-Carbon Bond Formation Based on Hydrogen Transfer, 27

2.3 Carbon-Nitrogen Bond Formation Based on Hydrogen Transfer and Dehydrogenation, 37

2.4 Carbon-Oxygen Bond Formation Based on Hydrogen Transfer and Dehydrogenation, 46

References, 52

Part ii ?4-Cyclopentadienone/?5-Hydroxycyclopentadienyl and Related Ligands in Transition Metal Catalyzed Hydrogen Transfer and Dehydrogenative Reactions 55

3 Oxidation and Hydrogenation Catalyzed by Transition Metal Complexes Bearing ?4-Cyclopentadienone/?5-Hydroxycyclopentadienyl and Related Ligands 57

3.1 Introduction, 57

3.2 Oxidation of Alcohol Based on Hydrogen Transfer and Dehydrogenation, 59

3.3 Oxidation of Amine Based on Hydrogen Transfer, 68

3.4 Hydrogenation and Transfer Hydrogenation of Carbonyl Compounds, 71

3.5 Hydrogenation and Transfer Hydrogenation of Imines and Related Compounds, 79

References, 84

4 Bond-Forming Reactions Catalyzed by Transition Metal Complexes Bearing ?4-Cyclopentadienone/?5-Hydroxycyclopentadienyl and Related Ligands 87

4.1 Introduction, 87

4.2 Carbon-Nitrogen Bond-Forming Reactions Based on Hydrogen Transfer and Dehydrogenation, 88

4.3 Carbon-Oxygen Bond-Forming Reactions Based on Hydrogen Transfer and Dehydrogenation, 97

4.4 Carbon-Carbon Bond-Forming Reactions Based on Hydrogen Transfer and Dehydrogenation, 102

References, 105

Part iii Pincer Ligands in Transition Metal Catalyzed Hydrogen Transfer and Dehydrogenative Reactions 107

5 Dehydrogenation of Alkanes Catalyzed by Transition Metal Complexes Bearing Pincer Ligands 109

5.1 Introduction, 109

5.2 Conversion of Alkanes into Alkenes Based on Hydrogen Transfer, 109

5.3 Dehydroaromatization of Alkanes Based on Hydrogen Transfer, 115

5.4 Alkane Metathesis by Tandem Alkane Dehydrogenation and Alkene Metathesis, 118

5.5 Conversion of Alkanes into Alkenes Based on Dehydrogenation, 121

References, 126

6 Oxidation and Hydrogenation Reactions Catalyzed by Transition Metal Complexes Bearing Pincer Ligands 128

6.1 Introduction, 128

6.2 Oxidation of Alcohols Based on Hydrogen Transfer and Dehydrogenation, 128

6.3 Dehydrogenation of Amines, 137

6.4 Hydrogenation and Transfer Hydrogenation of Carbon-Heteroatom Unsaturated Bonds, 141

References, 157

7 Bond-Forming Reactions Catalyzed by Transition Metal Complexes Bearing Pincer Ligands 159

7.1 Introduction, 159

7.2 Carbon-Carbon Bond Formation Based on Hydrogen Transfer, 159

7.3 Carbon-Nitrogen Bond Formation Based on Hydrogen Transfer and Dehydrogenation, 161

7.4 Carbon-Oxygen Bond Formation Based on Hydrogen Transfer and Dehydrogenation, 173

References, 182

Part iv Bidentate and Miscellaneous Ligands in Transition Metal Catalyzed Hydrogen Transfer and Dehydrogenative Reactions 183

8 Oxidation and Dehydrogenation of Alcohols and Amines Catalyzed by Well-Defined Transition Metal Complexes Bearing Bidentate and Miscellaneous Ligands 185

8.1 Introduction, 185

8.2 Oxidation of Alcohols Based on Hydrogen Transfer with Oxidant, 185

8.3 Dehydrogenative Oxidation of Alcohols without Oxidant, 209

8.4 Oxidation of Amines Based on Hydrogen Transfer and Dehydrogenation, 220

References, 224

9 Hydrogenation and Transfer Hydrogenation of Carbon-Heteroatom Unsaturated Bonds Catalyzed by Well-Defined Transition Metal Complexes Bearing Bidentate and Miscellaneous Ligands 228

9.1 Introduction, 228

9.2 Hydrogenation and Transfer Hydrogenation of Carbonyl and Related Compounds, 229

9.3 Hydrogenation and Transfer Hydrogenation of Imines and Related Compounds, 263

References, 274

10 Bond-Forming Reactions Based on Hydrogen Transfer Catalyzed by Well-Defined Transition Metal Complexes Bearing Bidentate and Miscellaneous Ligands 278

10.1 Introduction, 278

10.2 Carbon-Carbon Bond-Forming Reactions Based on Hydrogen Transfer, 279

10.3 Carbon-Nitrogen Bond-Forming Reactions Based on Hydrogen Transfer, 296

10.4 Carbon-Oxygen Bond-Forming Reactions Based on Hydrogen Transfer, 321

References, 330

Index 335