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Organometallic catalysis: some contributions to organic synthesis

Figure 1: A sampling of propargylamine-derived triazoles with therapeutic effects includes alpha-tetrasubstit Jump to Figure 1. Figure 2: A tetrasubstituted carbon bearing an amine red can provide fold increase in activity compared Jump to Figure 2. Scheme 1: KA 2 coupling followed by tandem silyl deprotection and triazole formation. Jump to Scheme 1. An identical yield is observed Jump to Scheme 2. Scheme 3: High overall yield of 1,2,3-triazole fully-substituted at the 4-position. Jump to Scheme 3. Scheme 1: Generation of iminyl radicals from oxime derivatives.

Scheme 2: Oxidative generation of iminyl radicals from N—H ketimines.

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Scheme 3: Copper-catalyzed aerobic reactions of in situ generated biaryl N—H ketimines. Jump to Scheme 4. Scheme 5: Proposed reaction mechanisms for the formation of 3a , 4a and 5a , and the reaction of hydroperoxide Jump to Scheme 5. Scheme 6: Formation of bromoketone 6e. Jump to Scheme 6.

Scheme 7: Electrophilic cyanation of Grignard reagents with pivalonitrile 1f. Jump to Scheme 7. Scheme 8: Electrophilic cyanation with pivalonitrile 1e. Jump to Scheme 8. Scheme 1: Structures of photoactivable click catalysts 1 — 3.

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Scheme 2: Syntheses of complexes 1 and 4. Figure 1: a Molecular structure of 4 a THF molecule present in the unit cell is not shown. Cu, green; C, g Figure 2: Evolution of the UV—vis spectra of deaerated freeze-pump-thaw degassed, sealed quartz cuvettes TH Scheme 3: Proposed mechanism for the photoreduction process. Jump to Figure 3. Figure 4: Reaction profiles for the formation of 9 under various illumination conditions: TLC lamp nm f Jump to Figure 4. Scheme 5: Preparative scale synthesis of 18 and Scheme 1: Standard reaction conditions.

Scheme 1: Examples of ferrocene derived drugs and ligands. Scheme 2: Structural types of ferrocene-based polymers. Scheme 3: Synthesis of ferrocene-derived alkenes from ferrocene carbaldehyde. Figure 1: Typical voltammogramms of vinylferrocenes 7 blue , 11 green , 12 red , anodic region. Figure 2: Typical voltammogramms of divinylferrocenes 10 black , 11 red , 12 blue , cathodic region.

Scheme 1: Use of a Chan—Lam reaction for the synthesis of tetrahydroquinolines and potential extension to pyr Scheme 2: Examples of pyridine synthesis from oxime precursors [51,52]. Scheme 3: Solvent effect on conversion of N -alkenylnitrones to pyridines. Scheme 4: Mechanistic experiments. Scheme 1: Copper-catalyzed C—H bond halogenation of 2-arylpyridine. Scheme 2: ortho -Chlorination of 2-arylpridines with acyl chlorides. Scheme 3: Copper-catalyzed chlorination of 2-arylpyridines using LiCl.

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Scheme 5: Copper-mediated selective C—H halogenations of 2-arylpyridine. Scheme 8: Copper-catalyzed quinoline C—H chlorination. Scheme 9: Copper-catalyzed arene C—H fluorination of benzamides. Jump to Scheme 9. Scheme Copper-catalyzed arene C—H iodination of 1,3-azoles. Jump to Scheme Scheme Copper-catalyzed C—H halogenations of phenols. Scheme Proposed mechanism for the C—H halogenation of phenols.

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Scheme Copper-catalyzed halogenation of electron enriched arenes. Scheme Copper-catalyzed C—H bromination of arenes. Scheme CuI-mediated synthesis of iododibenzo[ b , d ]furans via C—H functionalization. Scheme Cu-Mn spinel oxide-catalyzed phenol and heteroarene halogenation. Scheme Copper-catalyzed halogenations of 2-amino-1,3thiazoles. Scheme Copper-mediated chlorination and bromination of indolizines. Scheme Copper-catalyzed three-component synthesis of bromoindolizines.

Scheme Copper-mediated C—H halogenation of azacalix[1]arene[3]pyridines. Scheme Copper-mediated cascade synthesis of halogenated pyrrolones.

Scheme Copper-mediated alkene C—H chlorination in spirothienooxindole. Scheme Copper-catalyzed remote C—H chlorination of alkyl hydroperoxides. Scheme Copper-catalyzed C—H fluorination of alkanes. Scheme Copper-catalyzed or mediated C—H halogenations of active C sp 3 -bonds. Scheme 1: Reaction of organozinc compounds. Scheme 2: Proposed mechanism.

Scheme 1: Traditional activating mode and oxidative activation mode of free carboxylic acids in amide formati Scheme 2: Substrate scope for catalytic, direct amide formation from carboxylic acids and azoles. Reaction co Scheme 3: Further investigation into the scope of amine. Scheme 4: Possible transamidation process. Scheme 5: Scope of the amine transamidation from benzimidazole amides.

Reaction conditions: benzimidazole ami Scheme 6: Preparative scale of the reaction.


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Scheme 7: Radical scavenger reaction. Scheme 8: Control reactions. Scheme 9: Proposed mechanism. Scheme 1: Copper-catalyzed C—H amidation of tertiary amines. Scheme 2: Copper-catalyzed C—H amidation and sulfonamidation of tertiary amines. Scheme 3: Copper-catalyzed sulfonamidation of allylic C—H bonds. Scheme 4: Copper-catalyzed sulfonamidation of benzylic C—H bonds.

Scheme 5: Copper-catalyzed sulfonamidation of C—H bonds adjacent to oxygen. Scheme 6: Copper-catalyzed amidation and sulfonamidation of inactivated alkyl C—H bonds.


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Scheme 7: Copper-catalyzed amidation and sulfonamidation of inactivated alkanes. Scheme 8: Copper-catalyzed intramolecular C—H amidation for lactam synthesis. Scheme 9: Copper-catalyzed intramolecular C—H amidation for lactam synthesis. Scheme C—H amidation of pyridinylbenzenes and indoles.