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A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates

Identifieur interne : 001223 ( Main/Exploration ); précédent : 001222; suivant : 001224

A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates

Auteurs : Frédéric Leroux [France] ; Laurence Bonnafoux [France] ; Christophe Heiss [France] ; Françoise Colobert [France] ; Don Antoine Lanfranchi [France]

Source :

Advanced Synthesis & Catalysis [ 1615-4150 ] ; 2007-12-10.

RBID : ISTEX:252E46DC67C2FC99E026E4362FC0A53AA2FD6591

Descripteurs français

Wicri :
- topic : éthanol.

English descriptors

KwdEn :
- Aqueous solution, Aryllithium, Aryne, Aryne source, Biaryl, Biaryls, Biphenyl, Butyllithium, Catal, Chem, Chlorodicyclohexylphosphine, Colorless, Colorless cubes, Colorless needles, Column chromatography, Cyclohexane, Diethyl, Diethyl ether, Diphosphine ligands, Eluent, Ethanol, Ether, Gmbh, Hexane, Hours period, Kgaa, Leroux, Ligand, Mmol, Organic layers, Practical transition, Reaction mixture, Room temperature, Schlosser, Silica, Sodium sulfate, Sulfate, Synth, Tetrahydrofuran, Trisubstituted biaryls, Update, Updates scheme, Verlag, Verlag gmbh, Weinheim.
Teeft :
- Aqueous solution, Aryllithium, Aryne, Aryne source, Biaryl, Biaryls, Biphenyl, Butyllithium, Catal, Chem, Chlorodicyclohexylphosphine, Colorless, Colorless cubes, Colorless needles, Column chromatography, Cyclohexane, Diethyl, Diethyl ether, Diphosphine ligands, Eluent, Ethanol, Ether, Gmbh, Hexane, Hours period, Kgaa, Leroux, Ligand, Mmol, Organic layers, Practical transition, Reaction mixture, Room temperature, Schlosser, Silica, Sodium sulfate, Sulfate, Synth, Tetrahydrofuran, Trisubstituted biaryls, Update, Updates scheme, Verlag, Verlag gmbh, Weinheim.

Abstract

Upon treatment of various aryllithium intermediates with 1,2‐dibromobenzene or 1‐bromo‐2‐iodobenzene, dissymmetrical ortho,ortho′‐di‐, tri‐ and even tetrasubstituted bromo‐ or iodobiaryls become readily available. The crucial steps in all these reactions were the nucleophilic addition of the organolithium precursor to a transient aryne species released from it by β‐elimination of a lithium halide and, stabilization of the resulting 2‐biaryllithium intermediate by in situ transfer of bromine or iodine from the starting material. This straightforward transition metal‐free access to biaryls allows the preparation of highly valuable halobiaryls on a gram scale in excellent yields. These precursors can be subsequently functionalized by highly regioselective halogen/metal permutations into a vast variety of target molecules. This was demonstrated in the synthesis of several mono‐ and diphosphine ligands.

Url:

https://api.istex.fr/document/252E46DC67C2FC99E026E4362FC0A53AA2FD6591/fulltext/pdf

DOI: 10.1002/adsc.200700211

Affiliations:

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Le document en format XML

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<term>Chlorodicyclohexylphosphine</term>
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<term>Colorless needles</term>
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<front><div type="abstract" xml:lang="en">Upon treatment of various aryllithium intermediates with 1,2‐dibromobenzene or 1‐bromo‐2‐iodobenzene, dissymmetrical ortho,ortho′‐di‐, tri‐ and even tetrasubstituted bromo‐ or iodobiaryls become readily available. The crucial steps in all these reactions were the nucleophilic addition of the organolithium precursor to a transient aryne species released from it by β‐elimination of a lithium halide and, stabilization of the resulting 2‐biaryllithium intermediate by in situ transfer of bromine or iodine from the starting material. This straightforward transition metal‐free access to biaryls allows the preparation of highly valuable halobiaryls on a gram scale in excellent yields. These precursors can be subsequently functionalized by highly regioselective halogen/metal permutations into a vast variety of target molecules. This was demonstrated in the synthesis of several mono‐ and diphosphine ligands.</div>
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A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates

A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates

Source :

Descripteurs français

English descriptors

Abstract

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