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- Meta-selective_C-H_fuctionalization abstract "Meta-selective C-H functionalization refers to the regioselective reaction of a substituted aromatic ring on the C-H bond meta to the substituent.Substituted aromatic ring is an important type of substructure in pharmaceuticals and industrial compounds. Thus, synthetic methods towards substituted aromatic rings are always of great interest to chemists.Traditionally, regioselectivity on the aromatic ring is achieved by the electronic effect of substituents. Taking the well-known Friedel-Craft electrophilic aromatic substitution as example, electron donating groups direct the electrophile to ortho-/para-position while electron withdrawing groups direct the electrophile to meta-position. However, with complicated systems, electronic difference between different C-H bonds can be subtle and electronic directing effect alone could become less synthetically useful.The fast development of C-H activation in the past few decades provides synthetic chemists with the powerful tools to synthesize functionalized aromatic compounds with high selectivity. The widely used approach to achieve ortho-selectivity involves metal-chelating directing groups, which forms a relatively stable 6- or 7-membered cyclic pre-transition state to bring the metal catalyst to the proximity of the ortho-hydrogen. However, applying the same strategy to meta- or para- C-H functionalization does not work because the corresponding cyclophane-like cyclic pre-transition state is highly strained. Thus, while ortho-selectivity has been achieved by numerous catalytic systems, meta- and para-selectivity remains a challenge.In recent years, new strategies that override the electronic and steric bias have been developed to address meta-C-H functionalization. However, before these discoveries, synthesis of meta-substituted aromatic compounds could be either limited or cumbersome. For example, before the development of the C-H activation-involving one-pot synthetic route to meta-substituted phenol derivatives by Maleczka and co-workers, the traditional synthesis requires 10 steps from TNT. Some early attempts utilize steric and electronic effects to achieve meta-selectivity. However, they are either limited to certain structure of substrates or are not highly selective. In recent years, several highly selective meta-C-H functionalization strategies have been reported which can override the intrinsic electronic and steric properties of the substrates and can apply to a wide range of substrate derivatives. The development of the modern meta-C-H functionalization strategies “open doors for numerous possibilities” for synthesis and catalyst development.".
- Meta-selective_C-H_fuctionalization thumbnail Meta-selective_C-H_activation.gif?width=300.
- Meta-selective_C-H_fuctionalization wikiPageExternalLink FS13_SS14%5CPrakash_Kumar_Shee.pdf.
- Meta-selective_C-H_fuctionalization wikiPageID "44563594".
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- Meta-selective_C-H_fuctionalization wikiPageRevisionID "642576220".
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Amino_acid.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Anilide.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Aniline.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Anti-inflammatory_drugs.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Aromatic_hydrocarbon.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Aromatic_ring.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Aromaticity.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Baclofen.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Biphenyl.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Carbon–hydrogen_bond_activation.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Category:Organic_chemistry.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Cross-coupling.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Cyclophane.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Density_functional_theory.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Deprotonation.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Disproportionation.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Electron_donating_group.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Electron_withdrawing_group.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Electronic_effect.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Electrophile.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Electrophilic_aromatic_substitution.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Friedel–Crafts_reaction.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Hydrocinnamic_acid.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Ibruprofen.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Ibuprofen.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Medicinal_chemistry.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Metalation.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Naproxen.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Nitrile.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Nonsteroidal_anti-inflammatory_drug.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Nucleophile.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Oxidative_addition.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Pharmaceutical_drug.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Pharmaceuticals.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Phenylpropanoic_acid.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Polar_effect.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Rate-determining_step.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Reductive_elimination.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Regioselectivity.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Steric_effects.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Toluene.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Triflate.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink Trifluoromethanesulfonate.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Alternative_mechanism_of_copper_catalyzed_meta-selective_C-H_arylation.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Conventional_synthesis_involving_10_steps_and_TNT_starting_material.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Difficulty_in_achieving_meta-selectivity.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Highly_ortho_and_para_directing_m-OMe_overrides_the_meta-selectivity.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Mechanism_of_copper_catalyzed_meta-selective_C-H_arylation_involving_%22anti-oxy-cupration%22.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Meta-alkylation_achieved_by_remote_ortho-ruthenation_and_then_electrophilic-type_substitution.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Meta-selective_C-H_activation.gif.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Meta-selective_C-H_functionalization_on_bioactive_molecules.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Meta-selective_C-H_olefination_by_an_end-on_template.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:One-pot_synthesis_of_meta-phenol_derivative_involving_meta-C-H_activation.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Pd-Ag_dimeric_transition_state_vs_Pd_monomer_transition_state_for_meta-selective_C-H_activation.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Reaction_scheme_of_Ru_catalyzed_meta-selective_C-H_activation.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Reaction_scheme_of_copper_catalyzed_meta-selective_C-H_arylation_of_anilides.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:Reaction_scheme_of_copper_catalyzed_meta-selective_C-H_arylation_of_α-arylcarbonyl_compounds.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLink File:The_nitrile_group_helps_accommodate_the_highly_strained_cyclophane-like_pre-transition_state.jpg.
- Meta-selective_C-H_fuctionalization wikiPageWikiLinkText "Meta-selective C-H fuctionalization".
- Meta-selective_C-H_fuctionalization hasPhotoCollection Meta-selective_C-H_fuctionalization.
- Meta-selective_C-H_fuctionalization wikiPageUsesTemplate Template:Multiple_issues.
- Meta-selective_C-H_fuctionalization wikiPageUsesTemplate Template:Reflist.
- Meta-selective_C-H_fuctionalization subject Category:Organic_chemistry.
- Meta-selective_C-H_fuctionalization hypernym Type.
- Meta-selective_C-H_fuctionalization comment "Meta-selective C-H functionalization refers to the regioselective reaction of a substituted aromatic ring on the C-H bond meta to the substituent.Substituted aromatic ring is an important type of substructure in pharmaceuticals and industrial compounds. Thus, synthetic methods towards substituted aromatic rings are always of great interest to chemists.Traditionally, regioselectivity on the aromatic ring is achieved by the electronic effect of substituents.".
- Meta-selective_C-H_fuctionalization label "Meta-selective C-H fuctionalization".
- Meta-selective_C-H_fuctionalization sameAs m.012dtp4r.
- Meta-selective_C-H_fuctionalization wasDerivedFrom Meta-selective_C-H_fuctionalization?oldid=642576220.
- Meta-selective_C-H_fuctionalization depiction Meta-selective_C-H_activation.gif.
- Meta-selective_C-H_fuctionalization isPrimaryTopicOf Meta-selective_C-H_fuctionalization.