New PDF release: C-H Activation

By Andrew Martins, Brian Mariampillai, Mark Lautens (auth.), Jin-Quan Yu, Zhangjie Shi (eds.)

ISBN-10: 3642123554

ISBN-13: 9783642123559

Table of Contents - Synthesis within the Key of Catellani: Norbornene-Mediated ortho C–H Functionalization - Mechanistic concerns within the improvement and Use of Azine, Diazine and Azole N-Oxides in Palladium-Catalyzed Direct Arylation - Palladium and Copper Catalysis in Regioselective, Intermolecular Coupling of C–H and C–Hal Bonds - Pd-Catalyzed C–H Bond Functionalization at the Indole and Pyrrole Nucleus - distant C–H Activation through Through-Space Palladium and Rhodium Migrations - Palladium-Catalyzed Aryl–Aryl Bond Formation via Double C–H Activation - Palladium-Catalyzed Allylic C–H Bond Functionalization of Olefins - Ruthenium-Catalyzed Direct Arylations via C–H Bond Cleavages - Rhodium-Catalyzed C–H Bond Arylationof Arenes - Cross-Dehydrogenative Coupling Reactions of sp3-Hybridized C–H Bonds - Functionalization of Carbon–Hydrogen Bonds via Transition steel Carbenoid Insertion - Metal-Catalyzed Oxidations of C–H to C–N Bonds

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1 Synthetic Considerations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Reactivity with Azine and Diazine N-Oxides . . . . . . . . . . . . . . . . . . . . . 3 Regioselectivity with Nonsymmetrical Azine Substrates . . . . . . . . . . . . . . . 4 Azole N-Oxides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

37 2 Experimental Support of a Nonelectrophilic Aromatic Substitution Pathway in Palladium-Catalyzed Direct Arylation . . . . . . . . . . . . . . . . . . . . . . . . . 39 3 Azine and Azole N-Oxides in Direct Arylation . . . . . . . . . . . . . . . . . . . . . . 1 Synthetic Considerations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Reactivity with Azine and Diazine N-Oxides .

A fluorinated pyridine substrate may also be cross-coupled in high yield and it was also found that the site of arylation preferentially occurs adjacent to fluorine substituents when fewer fluorine atoms are present. Interestingly, the relative rates established from competition studies reveal that the rate of the direct arylation increases with the amount of fluorine substituents on the aromatic ring. In this way, it is inversely proportional to the arene nucleophilicity and therefore cannot arise from an electrophilic aromatic substitution type process (Scheme 7).

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C-H Activation by Andrew Martins, Brian Mariampillai, Mark Lautens (auth.), Jin-Quan Yu, Zhangjie Shi (eds.)


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