Directed Remote Aromatic Metalations: Mechanisms and Driving Forces
Identifieur interne : 005699 ( Main/Exploration ); précédent : 005698; suivant : 005700Directed Remote Aromatic Metalations: Mechanisms and Driving Forces
Auteurs : David Tilly [Australie, Niger, France] ; Jakob Magolan [États-Unis] ; Jacques Mortier [France]Source :
- Chemistry – A European Journal [ 0947-6539 ] ; 2012-03-26.
English descriptors
- KwdEn :
- Acid derivatives, Acidity, Amide, Amide bases, Amino group, Angew, Anion, Beak, Biaryl, Carboxylate, Castanet, Chem, Cipe, Cipe model, Collum, Complexation, Conformational constraints, Cyclization, Cyclized, Cyclized product, Derivative, Dmgs, Drem, Drem cyclization, Drem nucleophilic cyclization, Drem reactions, Electrophile, Electrophiles, Electrophilic, Electrophilic dmgs, External electrophiles, Fries, Gmbh, Hindrance, Hydrogen atoms, Inductive effects, Intramolecular, Intramolecular quenching, Isomerization, Kgaa, Kinetic control, Kinetically, Lateral, Lateral metalation, Lett, Lickor, Lithiated species, Lithiation, Lithium, Lithium base, Lithium bases, Lower temperatures, Magolan, Mechanistic, Metalated, Metalated species, Metalation, Metalations, Mild conditions, Mongin, Mortier, Nucleophilic, Optional site selectivity, Proximity effect, Pyridine, Pyridine nitrogen, Queguiner, Quenching, Reactant, Reaction conditions, Rearrangement, Regioselective, Regioselectivity, Remote anion, Remote anions, Remote hydrogen atoms, Remote metalation, Remote metalations, Remote position, Remote positions, Rigid substrates, Room temperature, Schlosser, Selectivity, Snieckus, Steric, Steric hindrance, Substituents, Tetrahedron, Tetrahedron lett, Tilly, Traces amount, Transition state, Transition structure, Verlag, Verlag gmbh, Wang, Weinheim, Weinheim chem.
- Teeft :
- Acid derivatives, Acidity, Amide, Amide bases, Amino group, Angew, Anion, Beak, Biaryl, Carboxylate, Castanet, Chem, Cipe, Cipe model, Collum, Complexation, Conformational constraints, Cyclization, Cyclized, Cyclized product, Derivative, Dmgs, Drem, Drem cyclization, Drem nucleophilic cyclization, Drem reactions, Electrophile, Electrophiles, Electrophilic, Electrophilic dmgs, External electrophiles, Fries, Gmbh, Hindrance, Hydrogen atoms, Inductive effects, Intramolecular, Intramolecular quenching, Isomerization, Kgaa, Kinetic control, Kinetically, Lateral, Lateral metalation, Lett, Lickor, Lithiated species, Lithiation, Lithium, Lithium base, Lithium bases, Lower temperatures, Magolan, Mechanistic, Metalated, Metalated species, Metalation, Metalations, Mild conditions, Mongin, Mortier, Nucleophilic, Optional site selectivity, Proximity effect, Pyridine, Pyridine nitrogen, Queguiner, Quenching, Reactant, Reaction conditions, Rearrangement, Regioselective, Regioselectivity, Remote anion, Remote anions, Remote hydrogen atoms, Remote metalation, Remote metalations, Remote position, Remote positions, Rigid substrates, Room temperature, Schlosser, Selectivity, Snieckus, Steric, Steric hindrance, Substituents, Tetrahedron, Tetrahedron lett, Tilly, Traces amount, Transition state, Transition structure, Verlag, Verlag gmbh, Wang, Weinheim, Weinheim chem.
Abstract
Directed remote aromatic metalations are useful synthetic transformations allowing for rapid regioselective access to elaborate highly substituted carbocyclic aromatic and heteroaromatic systems. This review unravels the tangle of data reported on directed remote aromatic metalations. Through a careful analysis of critically selected examples, advanced rationalizations of remote metalation regioselectivities are presented. These extend beyond the complex‐induced proximity effect (CIPE). Mechanisms, driving forces, and parameters influencing remote metalations are discussed. An understanding of these metalation mechanisms enables more accurate predictability of justification of regiochemical outcomes of these useful synthetic transformations.
Url:
DOI: 10.1002/chem.201103920
Affiliations:
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group</term><term>Angew</term><term>Anion</term><term>Beak</term><term>Biaryl</term><term>Carboxylate</term><term>Castanet</term><term>Chem</term><term>Cipe</term><term>Cipe model</term><term>Collum</term><term>Complexation</term><term>Conformational constraints</term><term>Cyclization</term><term>Cyclized</term><term>Cyclized product</term><term>Derivative</term><term>Dmgs</term><term>Drem</term><term>Drem cyclization</term><term>Drem nucleophilic cyclization</term><term>Drem reactions</term><term>Electrophile</term><term>Electrophiles</term><term>Electrophilic</term><term>Electrophilic dmgs</term><term>External electrophiles</term><term>Fries</term><term>Gmbh</term><term>Hindrance</term><term>Hydrogen atoms</term><term>Inductive effects</term><term>Intramolecular</term><term>Intramolecular quenching</term><term>Isomerization</term><term>Kgaa</term><term>Kinetic control</term><term>Kinetically</term><term>Lateral</term><term>Lateral metalation</term><term>Lett</term><term>Lickor</term><term>Lithiated species</term><term>Lithiation</term><term>Lithium</term><term>Lithium base</term><term>Lithium bases</term><term>Lower temperatures</term><term>Magolan</term><term>Mechanistic</term><term>Metalated</term><term>Metalated species</term><term>Metalation</term><term>Metalations</term><term>Mild conditions</term><term>Mongin</term><term>Mortier</term><term>Nucleophilic</term><term>Optional site selectivity</term><term>Proximity effect</term><term>Pyridine</term><term>Pyridine nitrogen</term><term>Queguiner</term><term>Quenching</term><term>Reactant</term><term>Reaction conditions</term><term>Rearrangement</term><term>Regioselective</term><term>Regioselectivity</term><term>Remote anion</term><term>Remote anions</term><term>Remote hydrogen atoms</term><term>Remote metalation</term><term>Remote metalations</term><term>Remote position</term><term>Remote positions</term><term>Rigid substrates</term><term>Room temperature</term><term>Schlosser</term><term>Selectivity</term><term>Snieckus</term><term>Steric</term><term>Steric hindrance</term><term>Substituents</term><term>Tetrahedron</term><term>Tetrahedron lett</term><term>Tilly</term><term>Traces amount</term><term>Transition state</term><term>Transition structure</term><term>Verlag</term><term>Verlag gmbh</term><term>Wang</term><term>Weinheim</term><term>Weinheim chem</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Acid derivatives</term><term>Acidity</term><term>Amide</term><term>Amide bases</term><term>Amino group</term><term>Angew</term><term>Anion</term><term>Beak</term><term>Biaryl</term><term>Carboxylate</term><term>Castanet</term><term>Chem</term><term>Cipe</term><term>Cipe model</term><term>Collum</term><term>Complexation</term><term>Conformational constraints</term><term>Cyclization</term><term>Cyclized</term><term>Cyclized product</term><term>Derivative</term><term>Dmgs</term><term>Drem</term><term>Drem cyclization</term><term>Drem nucleophilic cyclization</term><term>Drem reactions</term><term>Electrophile</term><term>Electrophiles</term><term>Electrophilic</term><term>Electrophilic dmgs</term><term>External electrophiles</term><term>Fries</term><term>Gmbh</term><term>Hindrance</term><term>Hydrogen atoms</term><term>Inductive effects</term><term>Intramolecular</term><term>Intramolecular quenching</term><term>Isomerization</term><term>Kgaa</term><term>Kinetic control</term><term>Kinetically</term><term>Lateral</term><term>Lateral metalation</term><term>Lett</term><term>Lickor</term><term>Lithiated species</term><term>Lithiation</term><term>Lithium</term><term>Lithium base</term><term>Lithium bases</term><term>Lower temperatures</term><term>Magolan</term><term>Mechanistic</term><term>Metalated</term><term>Metalated species</term><term>Metalation</term><term>Metalations</term><term>Mild conditions</term><term>Mongin</term><term>Mortier</term><term>Nucleophilic</term><term>Optional site selectivity</term><term>Proximity effect</term><term>Pyridine</term><term>Pyridine nitrogen</term><term>Queguiner</term><term>Quenching</term><term>Reactant</term><term>Reaction conditions</term><term>Rearrangement</term><term>Regioselective</term><term>Regioselectivity</term><term>Remote anion</term><term>Remote anions</term><term>Remote hydrogen atoms</term><term>Remote metalation</term><term>Remote metalations</term><term>Remote position</term><term>Remote positions</term><term>Rigid substrates</term><term>Room temperature</term><term>Schlosser</term><term>Selectivity</term><term>Snieckus</term><term>Steric</term><term>Steric hindrance</term><term>Substituents</term><term>Tetrahedron</term><term>Tetrahedron lett</term><term>Tilly</term><term>Traces amount</term><term>Transition state</term><term>Transition structure</term><term>Verlag</term><term>Verlag gmbh</term><term>Wang</term><term>Weinheim</term><term>Weinheim chem</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Directed remote aromatic metalations are useful synthetic transformations allowing for rapid regioselective access to elaborate highly substituted carbocyclic aromatic and heteroaromatic systems. This review unravels the tangle of data reported on directed remote aromatic metalations. Through a careful analysis of critically selected examples, advanced rationalizations of remote metalation regioselectivities are presented. These extend beyond the complex‐induced proximity effect (CIPE). Mechanisms, driving forces, and parameters influencing remote metalations are discussed. An understanding of these metalation mechanisms enables more accurate predictability of justification of regiochemical outcomes of these useful synthetic transformations.</div></front></TEI><affiliations><list><country><li>Australie</li><li>France</li><li>Niger</li><li>États-Unis</li></country><region><li>District fédéral central</li><li>Pays de la Loire</li></region><settlement><li>Le Mans</li><li>Moscou</li></settlement></list><tree><country name="Australie"><noRegion><name sortKey="Tilly, David" sort="Tilly, David" uniqKey="Tilly D" first="David" last="Tilly">David Tilly</name></noRegion></country><country name="Niger"><noRegion><name sortKey="Tilly, David" sort="Tilly, David" uniqKey="Tilly D" first="David" last="Tilly">David Tilly</name></noRegion></country><country name="France"><noRegion><name sortKey="Tilly, David" sort="Tilly, David" uniqKey="Tilly D" first="David" last="Tilly">David Tilly</name></noRegion><name sortKey="Mortier, Jacques" sort="Mortier, Jacques" uniqKey="Mortier J" first="Jacques" last="Mortier">Jacques Mortier</name><name sortKey="Mortier, Jacques" sort="Mortier, Jacques" uniqKey="Mortier J" first="Jacques" last="Mortier">Jacques Mortier</name></country><country name="États-Unis"><region name="District fédéral central"><name sortKey="Magolan, Jakob" sort="Magolan, Jakob" uniqKey="Magolan J" first="Jakob" last="Magolan">Jakob Magolan</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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