Nucleophilic and electrophilic platinum compounds for C-H bond activation - Table of Contents

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Nucleophilic and electrophilic platinum compounds for C-H bond activation

Duin, M.A.

Publication date

2004

Link to publication

Citation for published version (APA):

Duin, M. A. (2004). Nucleophilic and electrophilic platinum compounds for C-H bond

activation.

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Chapterr 1 General Introduction

1.11 Organometallic Chemistry 1 1.22 C-H Bond Activation of Hydrocarbons 2

1.2.11 C-H bond activation of hydrocarbons in homogeneous media 2 1.2.22 C-H bond activation of hydrocarbons by Pt(0)-systems 3 1.2.33 C-H activation by cationic platinum(II) species 5

1.33 Ligands Systems used in this Study 8

1.3.11 Imine ligands 8 1.3.22 N-Heterocyclic Carbene ligands 9

1.44 Aim, Scope and Outline of this Thesis 12

1.55 References 13

Chapterr 2, Part A Synthesis of new (o^-N.N'-DiazadieneHr^-alkene) platinum(O) compounds s

2.11 Introduction 19 2.22 Results and Discussion 21

2.2.11 Synthesis 21 2.2.22 Analysis 24 2.33 Conclusions 25 2.44 Experimental Section 25

2.4.11 General 25 2.4.22 Synthesis of R-DAB ligands 26

2.4.33 Synthesis of [Pt°(R-DAB)(ri2-alkene)] compounds 27

2.55 References 31

Chapterr 2, Part B Protonolysis of (diimine) platinum(O) alkene Compounds: A Routee to (Cationic) A Iky I Platinum(ll) Complexes?

2.66 Introduction 35 2.6.11 Hydrogen transfer from transition metal hydrides 35

TableTable of Contents

2.77 Results and Discussion 38

2.88 Conclusions 41 2.99 Experimental Section 41

2.9.11 General 41 2.9.22 Addition of Br0nsted acids to Pt(0)(NN)-complexes 42

2.100 References 42

Chapterr 3 Synthesis of Zerovalent Electron-rich Platinum Centers: Platinum(carbene)(alkene)22 Complexes

3.11 Introduction 45 3.22 Results and Discussion 46

3.2.11 Synthesis of zerovalent platinum(carbene)(alkene)2 complexes 46

3.2.22 Reactivity of platinum(carbene)(alkene)2 towards H2 54

3.33 Conclusions 57 3.44 Experimental Section 58

3.4.11 General 58 3.4.22 Synthesis 58 3.4.33 Crystal structure determination of la 62

3.4.44 Reactions with dihydrogen 63

3.55 References 63

Chapterr 4, Part A C-H Activation of Imidazolium Salts by Pt(0) Complexes at Ambientt Temperature: Synthesis of Hydrido Platinum Bis(carbene) Compounds

4.11 Introduction 67 4.22 Results and Discussion 69

4.2.11 C-H Activation of imidazolium salts by Pt(0) using Whitesides' method 69 4.2.22 C-H activation of imidazolium salts using Pt(0) carbene complexes 70

4.33 Conclusions 79 4.44 Experimental Section 80

4.4.11 General 80 4.4.22 Synthesis 80 4.4.33 In situ preparation of hydrido platinum bis(carbene) compounds 86

4.55 References 88

Chapterr 4, Part B In Situ Generated Cationic Platinum(ll) Complex for C-H Activationn of Hydrocarbons

4.66 Introduction 91 4.77 Results and Discussion 92

4.7.11 C-H activation of aromatic and aliphatic C-H bonds 92

4.7.22 Oxidation reactions 95 4.88 Conclusions 96 4.99 Experimental Section 96 4.9.11 General 96 4.9.22 NMR experiments 96 4.100 References 97

Chapterr 5 Platinum(ll) (NN) and Platinum(ll) (NNO) Complexes for C-H Activation n

5.11 Introduction 99 5.22 Results and Discussion 101

5.2.11 (NNO)-Ligand Synthesis 101 5.2.22 PtMe2(NNO) complexes with didentate N,N'-coordinated NNO ligands 103

5.2.33 Platinum(methyl) complexes with tridentate NNO-ligands 104

5.33 Conclusions 108 5.44 Experimental Section 109

5.4.11 General 109 5.4.22 Synthesis 109 5.4.33 C-H bond activation experiments 120

5.55 References 121

Summaryy 123 Samenvattingg 129 Dankwoordd 135