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Review
. 2010 Feb 10;110(2):1147-69.
doi: 10.1021/cr900184e.

Palladium-catalyzed ligand-directed C-H functionalization reactions

Affiliations
Review

Palladium-catalyzed ligand-directed C-H functionalization reactions

Thomas W Lyons et al. Chem Rev. .
No abstract available

PubMed Disclaimer

Figures

Figure 1
Figure 1
Key Mechanistic Data for PdCl2-Catalyzed Chlorination 2-ortho-Tolylpyridine with NCS
Scheme 1
Scheme 1
Representative PdII/0 Catalytic Cycle for C–H Functionalization
Scheme 2
Scheme 2
Mechanism Involving Direct Electrophilic Functionalization of Complex A
Scheme 3
Scheme 3
Mechanism Involving One Electron Oxidation of Complex A
Scheme 4
Scheme 4
Mechanism Involving Two Electron Oxidation of Complex A
Scheme 5
Scheme 5
Pd(OAc)2-Catalyzed sp2 C–H Acetoxylation with PhI(OAc)2
Scheme 6
Scheme 6
Pd(OAc)2-Catalyzed sp3 C–H Acetoxylation with PhI(OAc)2,,
Scheme 7
Scheme 7
Proposed Mechanism for Pd(OAc)2-Catalyzed C–H Acetoxylation with PhI(OAc)2,
Scheme 8
Scheme 8
Proposed Competing Mechanisms of Rate-Limiting Cyclopalladation during Pd(OAc)2-Catalyzed C–H Acetoxylation
Scheme 9
Scheme 9
Formation and Reactivity of Model PdIV Complex 8
Scheme 10
Scheme 10
Pd(OAc)2-Catalyzed sp2 C–H Bond Oxygenation with Inorganic Peroxides,
Scheme 11
Scheme 11
Acetoxylation of sp3 C–H Bonds with Oxone
Scheme 12
Scheme 12
Oxazoline-Directed sp3 C–H Acetoxylation with MeCO2Ot-Bu or Lauroyl Peroxide
Scheme 13
Scheme 13
Intermolecular C–S Bond Formation with ArSO2Cl
Scheme 14
Scheme 14
Halogenation of sp2 C–H Substrates with N-Halosuccinimides
Scheme 15
Scheme 15
Complementary Halogenation Products in Presence/Absence of Pd
Scheme 16
Scheme 16
Oxidation with N-Chlorosuccinimide and C–Cl Bond-Forming Reductive Elimination from a PdIV Model Complex
Scheme 17
Scheme 17
Oxidation of 4 with PhICl2
Scheme 18
Scheme 18
sp3 C–H Iodination with IOAc (Formed in situ from PhI(OAc)2/I2)
Scheme 19
Scheme 19
Electrophilic Fluorinating Reagents for the Benzylic Fluorination of 8-Methylquinoline
Scheme 20
Scheme 20
Pd(OAc)2-Catalyzed ortho-Fluorination of 2-Arylpyridines with N-Fluoropyridinium Tetrafluoroborate
Scheme 21
Scheme 21
Intramolecular C–H Amination to Form Carbazoles
Scheme 22
Scheme 22
Proposed PdII/0 Mechanisms for Carbazole Formation,
Scheme 23
Scheme 23
Intramolecular C–H Amination to Form Lactams
Scheme 24
Scheme 24
Intermolecular Amination of Pyridines and Oxime Ethers
Scheme 25
Scheme 25
Pd(OAc)2 Catalyzed sp2 C–H Phenylation with [Ph2I]BF4
Scheme 26
Scheme 26
Key Steps in the Proposed Mechanism of sp2 C–H Arylation with [Mes–I–Ph]BF4
Scheme 27
Scheme 27
Pd(OAc)2-Catalyzed sp2 C–H Arylation with AgOAc/Ar-I,–
Scheme 28
Scheme 28
Pd(OAc)2-Catalyzed sp3 C–H Arylation with AgOAc/Ar-I,
Scheme 29
Scheme 29
Proposed Mechanism for Pd-Catalyzed Directed Arylation with AgI/Ar-I
Scheme 30
Scheme 30
PdII/0-Catalyzed ortho-Arylation of Benzoic Acids with Ar-Cl
Scheme 31
Scheme 31
PdII/0-Catalyzed sp3 Arylation of Alkylamides with Ar-I
Scheme 32
Scheme 32
Proposed Mechanism for PdII/IV Homocoupling of Arylpyridines
Scheme 33
Scheme 33
Pd-Catalyzed Benzoquinone-Promoted Oxidative L~C–H/Ar–H Cross-Coupling
Scheme 34
Scheme 34
Tuning Site-Selectivity of L~C–H/Ar–H Cross-Coupling by Variation of Quinone Promoter
Scheme 35
Scheme 35
Oxidative Cross-Coupling of Amide Derivatives with Aryl–H using Cu(OTf)2/O2 as Oxidant
Scheme 36
Scheme 36
Oxidative Cross-Coupling of Amide Derivatives with Ar–H using O2 as Oxidant
Scheme 37
Scheme 37
Proposed Mechanism for L~C–H/Ar–H Cross-Coupling–,
Scheme 38
Scheme 38
ortho-Alkenylation of Benzylamines with α,β-Unsaturated Esters and Amides
Scheme 39
Scheme 39
ortho-Alkylation of Oxazolines with SnR4
Scheme 40
Scheme 40
Pd-Catalyzed Ethoxycarbonylation with DEAD
Scheme 41
Scheme 41
Effect of Galvinoxyl on Stoichiometric Ethoxycarbonylation

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