Table of Contents

Cover

Title Page

Chapter 1: Oxidative Coupling – Bonding between Two Nucleophiles

1.1 Introduction/General
References

Chapter 2: Organometals as Nucleophiles

2.1 Classification and Applications of Organometallic Reagents
2.2 Csp–M and Csp–M as Nucleophiles
2.3 Csp–M and Csp²–M as Nucleophiles
2.4 Csp–M and Csp³–M as Nucleophiles
2.5 Csp²–M and Csp²–M as Nucleophiles
2.6 Csp²–M and Csp³–M as Nucleophiles
2.7 Csp³–M and Csp³–M as Nucleophiles
2.8 Conclusions
Acknowledgments
References

Chapter 3: Oxidative Couplings Involving the Cleavage of C–H Bonds

3.1 Theoretical Understandings and Methods in C–H Bond Functionalization
3.2 Oxidative Couplings between Organometals and Hydrocarbons
3.3 Oxidative Couplings between Two Hydrocarbons
3.4 Conclusions
References

Chapter 4: Bonding Including Heteroatoms via Oxidative Coupling

4.1 Introduction
4.2 Oxidative C–O Bond Formation
4.3 Oxidative C–N Bond Formation
4.4 Oxidative C–Halo Bond Formation
4.5 Oxidative C–S Bond Formation
4.6 Oxidative C–P Bond Formation
4.7 Oxidative C–B Bond Formation
References

Chapter 5: Oxidative Radical Couplings

5.1 Introduction
5.2 Oxidative Radical C–C Couplings
5.3 Oxidative Radical C–C Couplings through Cascade Process
5.4 Oxidative Radical C–C Couplings via C–C(N) Bond Cleavage
References

Index

End User License Agreement

List of Illustrations

Chapter 1: Oxidative Coupling – Bonding between Two Nucleophiles

Scheme 1.1 Bond formation modes of classic cross-coupling and oxidative cross-coupling.
Scheme 1.2 Comparison between classic synthetic route and oxidative cross-coupling.
Scheme 1.3 General catalytic cycle of palladium-catalyzed oxidative cross-coupling reactions.

Chapter 2: Organometals as Nucleophiles

Scheme 2.1 Typical elements in organometallic reagents.
Scheme 2.2 Different oxidative cross-coupling reactions.
Scheme 2.3
Scheme 2.4
Scheme 2.5
Scheme 2.6
Scheme 2.7 Triynes from TBS protected diynes.
Scheme 2.8 Oxidative homocoupling of alkynylsilanes to form diynes.
Scheme 2.9 Pd catalyzed homocoupling of alkylylsilanes without activator.
Scheme 2.10 Homocoupling of alkynyltrimethyltin reagent to form polymers.
Scheme 2.11 Mechanism of oxidative homocoupling of alkynyltin reagents.
Scheme 2.12 Palladium-catalyzed homocoupling of alkynylborates.
Scheme 2.13 Oxidative homocoupling of alkynyltrifluoroborates.
Scheme 2.14 Proposed mechanism of the oxidative homocoupling of alkynyltrifluoroborates.
Scheme 2.15 Manganese-catalyzed homocoupling of alkynyl Grignard reagents.
Scheme 2.16 Proposed mechanism of the Mn-catalyzed reaction.
Scheme 2.17 Oxidative cross-coupling of alkynyl magnesium reagents.
Scheme 2.18 Iron catalyzed homocoupling of alkynyl Grignard reagents.
Scheme 2.19 Knochel's protocol to form diynes.
Scheme 2.20 Homocoupling of alkynyl Grignard reagents without transition metals.
Scheme 2.21 Homocoupling reaction of functionalized n-butyl alkynyltellurides.
Scheme 2.22 Proposed mechanism for the homocoupling of functionalized n-butyl alkynyltellurides.
Scheme 2.23 General mechanism of Sonogashira coupling reaction.
Scheme 2.24 Oxidative coupling between aryl magnesium reagents and alkynyl lithium.
Scheme 2.25 Examples of substrate scope.
Scheme 2.26 Mechanism of the Mn-catalyzed oxidative cross-coupling.
Scheme 2.27 Manganese-catalyzed oxidative cross-coupling between aryl and alkynyl Grignard reagents.
Scheme 2.28 Differences of reaction rate for aryl and alkynyl Grignard reagents.
Scheme 2.29 Substrate scope.
Scheme 2.30 Oxidative cross-coupling between alkyl zinc and alkynyl tin.
Scheme 2.31 Mechanism.
Scheme 2.32 CO accelerated oxidative cross-coupling of alkyl zinc reagents and terminal alkynes.
Scheme 2.33
Scheme 2.34 Vanadium catalyzed synthesis of unsymmetrical biaryls.
Scheme 2.35 Iron-catalyzed oxidative cross-coupling to form biaryls.
Scheme 2.36 Ligand effect in Pd catalyzed oxidative cross-coupling.
Scheme 2.37 Substrate scope of the oxidative cross-coupling.
Scheme 2.38 Csp²–Zn cross-coupled with Csp³–In.
Scheme 2.39 Mechanism for the coupling of Csp²–Zn and Csp³–In.
Scheme 2.40
Scheme 2.41
Scheme 2.42
Scheme 2.43 Homocoupling of alkyl zinc reagents.
Scheme 2.44 β-H elimination effect.
Scheme 2.45 Mechanism of the homocoupling.
Scheme 2.46

Chapter 3: Oxidative Couplings Involving the Cleavage of C–H Bonds

Scheme 3.1 Five typical mechanisms for inner-sphere transition metal-mediated C–H bond cleavage.
Scheme 3.2 Two typical mechanisms for outer-sphere transition metal-mediated C–H bond cleavage.
Scheme 3.3 Oxidative addition between iridium and C–H bond in simple alkanes.
Scheme 3.4 Mechanism for the aromatic borylation catalyzed by iridium species.
Scheme 3.5 Ru(0)-catalyzed ortho-C–H functionalization via oxidative addition.
Scheme 3.6 Electrophilic aromatic mercuration.
Scheme 3.7 The Fujiwara–Moritani reaction.
Scheme 3.8 Direct C-2 arylation of indoles with aryl iodides at room temperature.
Scheme 3.9 σ-Bond metathesis pathway.
Scheme 3.10 Representative mechanism for the acetolysis of diphenylmercury(II).
Scheme 3.11 Mechanism for the cyclometalation of DMBA-H with palladium.
Scheme 3.12 Proposed catalytic cycle for direct arylation via CMD mechanism.
Scheme 3.13 Addition of methane to [ZrN] double bond.
Scheme 3.14 Biomimetic C–H oxidation of cyclohexane using nonheme Fe(II) complex.
Scheme 3.15 Catalytic cycle for metal-catalyzed carbenoid insertion into a C–H bond.
Scheme 3.16 Rh₂(4S-MEOX)₄-catalyzed stereoselective carbenoid insertion into a C–H bond.
Scheme 3.17 Rh₂(S-NTTL)₄-catalyzed stereoselective nitrenoid insertion into a C–H bond.
Scheme 3.18 Total synthesis of (−)-tetrodotoxin via both carbenoid and nitrenoid insertion reactions.
Scheme 3.19 Directed C–H bond functionalization.
Scheme 3.20 Preparation of celecoxib analogs via divergent C–H functionalization.
Scheme 3.21 meta-Selective C–H functionalization approaches.
Scheme 3.22 Directing groups for the Pd-catalyzed C(sp³)–H functionalization.
Scheme 3.23 Pd-catalyzed enantioselective C–H functionalization.
Scheme 3.24 C–H borylation of disubstituted arenes.
Scheme 3.25 Overview of the C–H functionalization via ionic intermediates.
Scheme 3.26 α-Cyanation of amines via iminium cation.
Scheme 3.27 Copper-catalyzed CDC α-alkynylation of amine.
Scheme 3.28 General mechanism of copper-catalyzed CDC α-alkynylation of amine.
Scheme 3.29 Intramolecular radical reactions.
Scheme 3.30 C–H functionalization via radical intermediates.
Scheme 3.31 Transition metal-catalyzed radical oxidative cross-coupling reactions.
Scheme 3.32 Amine-catalyzed enantioselective α-arylation of aldehydes.
Scheme 3.33 Proposed mechanism for amine-catalyzed enantioselective α-arylation.
Scheme 3.34 Photoredox-catalyzed C–H arylation reaction.
Scheme 3.35 C(sp)–C(sp³) oxidative coupling between terminal alkynes and alkylzinc reagents.
Scheme 3.36 Oxidative coupling between terminal alkynes and cuprous cyanide.
Scheme 3.37 Copper-mediated aerobic trifluoromethylation of terminal alkynes.
Scheme 3.38 Oxidative cross-coupling between Csp²–H and organometals.
Scheme 3.39 Rh-catalyzed oxidative coupling between 2-phenylpridine and aryl stannanes.
Scheme 3.40 Stoichiometric experiments.
Scheme 3.41 Oxidative cross-coupling between directing-group-containing arenes and alkylstannane reagents.
Scheme 3.42 Pd-catalyzed oxidative coupling between simple arenes and arylstannanes.
Scheme 3.43 Pd-catalyzed oxidative cross-coupling of pyridine-directed arenes with both methylboroxine and alkylboronic acids.
Scheme 3.44 Pd-catalyzed oxidative coupling of benzoic acids/aryl acetic acids with aryltrifluoroborates.
Scheme 3.45 Pd-catalyzed oxidative cross-coupling between arylboronic acids and acetamido-containing arenes.
Scheme 3.46 Pd-catalyzed oxidative coupling of electron-rich arenes with arylboronic acid.
Scheme 3.47 Mn-mediated oxidative coupling of simple arenes with arylboronic acid.
Scheme 3.48 Cu-promoted oxidative cross-coupling of electron-rich arenes and arylboronic acids.
Scheme 3.49 Fe-mediated oxidative coupling of unactivated arenes with arylboronic acid.
Scheme 3.50 Fe-mediated oxidative coupling of N-heterocyclics with arylboronic acid.
Scheme 3.51 Fe-catalyzed oxidative coupling of arylboronic acids with benzene derivatives.
Scheme 3.52 Pd-catalyzed oxidative arylation of electron-deficient arenes with arylboronic acids.
Scheme 3.53 Ni-catalyzed oxidative cross-coupling between heteroarenes and arylboronic acids.
Scheme 3.54 Pd-catalyzed oxidative cross-coupling between polycyclic aromatic hydrocarbons and arylboroxins.
Scheme 3.55 Synthesis of extended PAHs.
Scheme 3.56 Pd-catalyzed oxidative C4-arylation of thiophenes with arylboronic acids.
Scheme 3.57 Pd-catalyzed oxidative coupling between acetamido-group-directing ortho-C–H bond and trialkoxyarylsilanes.
Scheme 3.58 Ni-catalyzed oxidative coupling between heteroarenes and arylsilanes/alkenylsilane.
Scheme 3.59 Pd-catalyzed oxidative coupling between thiophenes and benzothiophenes and aryltrimethylsilanes.
Scheme 3.60 Fe-catalyzed oxidative cross-couplings between Csp²–H and organozinc reagents.
Scheme 3.61 Fe-catalyzed oxidative cross-couplings between aryl imines and organozinc reagents.
Scheme 3.62 Fe-catalyzed oxidative couplings between alkenes and organozinc reagents.
Scheme 3.63 Fe-catalyzed oxidative couplings between alkenes and Grignard reagents.
Scheme 3.64 Co-catalyzed oxidative cross-couplings between benzo[h]quinoline and Grignard reagents.
Scheme 3.65 Co-catalyzed oxidative couplings between arylpyridines and Grignard reagents.
Scheme 3.66 Ni-catalyzed alkenylation of arylboronic acids with olefins.
Scheme 3.67 Cyanation of Csp³–H bonds besides N atoms.
Scheme 3.68 Arylation of Csp³–H bonds.
Scheme 3.69 Arylation of unactivated Csp³–H bonds.
Scheme 3.70 Glaser coupling and Glaser–Hay coupling.
Scheme 3.71 Dimeric copper acetylide mechanism.
Scheme 3.72 Cu(II)–Cu(I) synergistic cooperation to lead the cleavage of acetylene C–H bond and oxidative homocoupling.
Scheme 3.73 Ni- and Cu-catalyzed oxidative cross-coupling of different terminal alkynes.
Scheme 3.74 Gold-catalyzed oxidative cross-coupling of different terminal alkynes.
Scheme 3.75 Gold-mediated coupling between arenes and terminal alkynes.
Scheme 3.76 Gold-catalyzed alkynylation of electron-rich arenes and alkenes.
Scheme 3.77 Proposed mechanism for the Au-catalyzed alkynylation of electron-rich arenes.
Scheme 3.78 Pd-catalyzed C2-alkynylation of N-protected indoles with terminal alkynes.
Scheme 3.79 Direct alkynylation of thiophenes and other aromatic heterocycles.
Scheme 3.80 Direct oxidative C–H alkynylation of electron-poor (hetero)arenes.
Scheme 3.81 Directed C–H alkynylation of unactivated (hetero)arenes.
Scheme 3.82 Oxidative coupling between acetylene C–H bonds and C(sp³)–H bonds adjacent to heteroatoms.
Scheme 3.83 Tandem oxidative C(sp³)–H/C(sp)–H alkynylation and cyclization.
Scheme 3.84 Oxidative cross-coupling using Csp²–H and Csp²–H as nucleophiles.
Scheme 3.85 Oxidative cross-coupling between benzoquinoline (Bzq) and benzene.
Scheme 3.86 Oxidative coupling of unactivated arenes with arenes containing an acetamino group.
Scheme 3.87 Oxidative coupling of unactivated arenes with pyridine N-oxides.
Scheme 3.88 Oxidative cross-coupling of different unactivated arenes.
Scheme 3.89 Pd-catalyzed oxidative C-3 arylation of indoles.
Scheme 3.90 Pd-catalyzed oxidative C-2 arylation of indoles.
Scheme 3.91 Pd-catalyzed oxidative C-2 arylation of benzofuran.
Scheme 3.92
Scheme 3.93
Scheme 3.94 Pd-catalyzed intramolecular oxidative cyclization of N-benzoylindoles.
Scheme 3.95 Pd-catalyzed intramolecular oxidative cyclization of diarylethers and diarylanilines.
Scheme 3.96 Pd-catalyzed one-pot synthesis of carbazoles from aryl triflates and anilines.
Scheme 3.97 Pd-catalyzed oxidative cyclization of anilides.
Scheme 3.98 Pd-catalyzed intramolecular oxidative cyclization.
Scheme 3.99 Oxidative coupling to form annulated seven-membered rings.
Scheme 3.100 Oxidative coupling to form annulated eight-membered rings.
Scheme 3.101 Represented substrates in oxidative Heck-type couplings.
Schemes 3.102 General mechanisms for Pd-catalyzed oxidative Heck-type alkenylation by intermolecular carbopalladation.
Scheme 3.103 General mechanisms for Pd-catalyzed oxidative Heck-type alkenylation by aromatic C–H palladation.
Scheme 3.104 Pd-catalyzed oxidative ortho-alkenylation of anilides at room temperature.
Scheme 3.105
Scheme 3.106
Scheme 3.107
Scheme 3.108
Scheme 3.109
Scheme 3.110
Scheme 3.111
Scheme 3.112
Scheme 3.113
Scheme 3.114
Scheme 3.115
Scheme 3.116
Scheme 3.117
Scheme 3.118
Scheme 3.119
Scheme 3.120
Scheme 3.121
Scheme 3.122
Scheme 3.123
Scheme 3.124
Scheme 3.125
Scheme 3.126
Scheme 3.127
Scheme 3.128
Scheme 3.129

Chapter 4: Bonding Including Heteroatoms via Oxidative Coupling

Scheme 4.1
Scheme 4.2
Scheme 4.3
Scheme 4.4
Scheme 4.5
Scheme 4.6
Scheme 4.7
Scheme 4.8
Scheme 4.9
Scheme 4.10
Scheme 4.11
Scheme 4.12
Scheme 4.13
Scheme 4.14
Scheme 4.15
Scheme 4.16
Scheme 4.17
Scheme 4.18
Scheme 4.19
Scheme 4.20
Scheme 4.21
Scheme 4.22
Scheme 4.23
Scheme 4.24
Scheme 4.25
Scheme 4.26
Scheme 4.27
Scheme 4.28
Scheme 4.29
Scheme 4.30
Scheme 4.31
Scheme 4.32
Scheme 4.33
Scheme 4.34
Scheme 4.35
Scheme 4.36
Scheme 4.37
Scheme 4.38
Scheme 4.39
Scheme 4.40
Scheme 4.41
Scheme 4.42
Scheme 4.43
Scheme 4.44
Scheme 4.45
Scheme 4.46
Scheme 4.47
Scheme 4.48
Scheme 4.49
Scheme 4.50
Scheme 4.51
Scheme 4.52
Scheme 4.53
Scheme 4.54
Scheme 4.55
Scheme 4.56
Scheme 4.57
Scheme 4.58
Scheme 4.59
Scheme 4.60
Scheme 4.61
Scheme 4.62
Scheme 4.63
Scheme 4.64
Scheme 4.65
Scheme 4.66
Scheme 4.67
Scheme 4.68
Scheme 4.69
Scheme 4.70
Scheme 4.71
Scheme 4.72
Scheme 4.73
Scheme 4.74
Scheme 4.75
Scheme 4.76
Scheme 4.77
Scheme 4.78
Scheme 4.79
Scheme 4.80
Scheme 4.81
Scheme 4.82
Scheme 4.83
Scheme 4.84
Scheme 4.85
Scheme 4.86

Chapter 5: Oxidative Radical Couplings

Scheme 5.1 Oxidative C–C couplings.
Scheme 5.2
Scheme 5.3 Alkynylation of tertiary amines.
Scheme 5.4 Alkynylation of diphenylmethane derivatives.
Scheme 5.5 Methylation of 2-phenylpyridines.
Scheme 5.6 Oxidative coupling of arenes with simple nonactivated alkanes.
Scheme 5.7 Oxidative Pd-catalyzed ortho-aroylation.
Scheme 5.8 Oxidative cross-coupling of acetanilide and toluene.
Scheme 5.9 Proposed generation of acyl radicals.
Scheme 5.10 Oxidative cross-coupling of acetanilide and toluene.
Scheme 5.11 Para-selective oxidative cross-coupling of substituted benzene with cycloalkanes.
Scheme 5.12 Oxidative cross-coupling of pyridine N-oxide derivatives with simple alkanes.
Scheme 5.13 Oxidative C-2 alkylation of quinoline N-oxides with ethers.
Scheme 5.14 Oxidative coupling of α-position sp³ C–H in alcohols and ethers.
Scheme 5.15 Oxidative radical coupling between simple ethers and α,α-diaryl allylic alcohols.
Scheme 5.16 Proposed mechanism for oxidative radical coupling.
Scheme 5.17 Oxidative radical coupling between amides/ethers and benzene derivatives.
Scheme 5.18 Proposed mechanism for oxidative radical coupling.
Scheme 5.19 Nickel-catalyzed regioselective coupling of dioxane with indoles.
Scheme 5.20 Oxindole synthesis through Pd-catalysis or oxidative coupling.
Scheme 5.21 Cu-mediated intramolecular oxidative C–C bond formation.
Scheme 5.22 Cu-mediated oxindole synthesis.
Scheme 5.23 Proposed mechanism for oxidative radical coupling for oxindole synthesis.
Scheme 5.24 Oxidative coupling/cyclization of alkenes and 2-(pyridin-2-yl) acetate derivatives.
Scheme 5.25 Proposed mechanism for oxidative radical coupling for indolizine synthesis.
Scheme 5.26 Oxidative coupling/annulation of β-keto esters with alkenes.
Scheme 5.27 A radical addition/cyclization mechanism.
Scheme 5.28 Copper-catalyzed oxidative coupling of enones and toluenes.
Scheme 5.29 A proposed reaction pathway for the oxidative coupling.
Scheme 5.30 Oxidative coupling of benzylic C–H bonds with 1,3-dicarbonyl compounds.
Scheme 5.31 Intramolecular kinetic isotope effect.
Scheme 5.32 Fe-catalyzed alkylation of activated methylenes.
Scheme 5.33 Proposed mechanism for alkylation of activated methylenes.
Scheme 5.34 Oxidative coupling of vinylarenes with cyclic ethers.
Scheme 5.35 Oxidative cross-coupling between benzylic C–H and 1-aryl vinyl acetate.
Scheme 5.36 Oxidative radical coupling of substituted olefins and simple ethers.
Scheme 5.37 Oxidative cross-coupling of different phenols.
Scheme 5.38 Ortho-C–H acylation of 2-arylpyridines with arylmethyl amines.
Scheme 5.39 Proposed process for generation of radical intermediates.
Scheme 5.40 Oxidative coupling of alkenes with aldehydes.
Scheme 5.41 Oxidative coupling of arenes and alkenes.
Scheme 5.42 Proposed mechanism for the oxidative cross-coupling between 1,3,5-trimethoxybenzene and diarylethylenes.
Scheme 5.43 Oxidative coupling of isonitrile with simple alkanes.
Scheme 5.44 Proposed mechanism for the free-radical addition/cyclization cascade reaction.
Scheme 5.45 Oxidative radical C–C coupling can proceed between 2-aryl phenyl isonitrile and simple alcohols.
Scheme 5.46 Coupling between 2-aryl phenyl isonitrile and dioxane.
Scheme 5.47 Functionalized oxindole synthesis via oxidative radical coupling.
Scheme 5.48 Oxidative tandem coupling of activated alkenes with carbonyl C(sp²)–H bonds.
Scheme 5.49 Tandem radical addition/cyclization of acrylamides and benzyl hydrocarbons.
Scheme 5.50 Proposed mechanism for the tandem radical addition/cyclization of acrylamides and benzyl hydrocarbons.
Scheme 5.51 Reaction of activated alkenes and alcohols.
Scheme 5.52 Proposed mechanism for the metal-free tandem radical addition/cyclization reaction of activated alkenes and alcohols.
Scheme 5.53 Oxidative cyclization of acrylamides with 1,3-dicarbonyls.
Scheme 5.54 Oxidative coupling of hydroxymethylacrylamide with 1,3-dicarbonyl compounds.
Scheme 5.55 Oxidative alkylarylation of acrylamides with simple alkanes.
Scheme 5.56 Reaction mechanism for free radical cascade process.
Scheme 5.57 Diacylation of coumarins.
Scheme 5.58 Decarboxylative acylation of acrylamides.
Scheme 5.59 Decarboxylative acylation of acrylamides to yield six-membered rings.
Scheme 5.60 Decarbonylative coupling of aromatic aldehydes with arenes.
Scheme 5.61 Oxidative coupling of styrenes and benzyl alcohols with arenes.
Scheme 5.62 Arylalkoxycarbonylation of N-aryl acrylamides.
Scheme 5.63 Radical arylalkoxycarbonylation of 2-isocyanobiphenyl.
Scheme 5.64 Arylalkoxycarbonylation of imidazoheterocycles.

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