Mild and Efficient Copper-Catalyzed Cyanation of Aryl Iodides and Bromides
An efficient copper‐catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen‐ and/or oxygen‐binding sites, have never previously been used in this type of reaction. A prot...
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| Published in | Chemistry : a European journal Vol. 11; no. 8; pp. 2483 - 2492 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
08.04.2005
WILEY‐VCH Verlag Wiley Wiley-VCH Verlag |
| Subjects | |
| Online Access | Get full text |
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| Abstract | An efficient copper‐catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen‐ and/or oxygen‐binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper‐catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110 °C) compared with the Rosenmund–von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper‐mediated cyanation reactions.
The high‐yielding cyanation of aryl iodides and bromides is efficiently performed by using catalytic amounts of copper salts and bi‐, tri‐, or tetradentate ligands. The cyanation of aryl bromides is achieved by the copper‐catalyzed in situ production of the corresponding aryl iodides in the presence of catalytic amounts of potassium iodide (see scheme). This protocol involves two main innovations: 1) the use of catalytic amounts of ligands and 2) the use of acetone cyanohydrin as the cyanating agent in copper‐mediated cyanation reactions. |
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| AbstractList | An efficient copper‐catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen‐ and/or oxygen‐binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper‐catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110 °C) compared with the Rosenmund–von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper‐mediated cyanation reactions.
The high‐yielding cyanation of aryl iodides and bromides is efficiently performed by using catalytic amounts of copper salts and bi‐, tri‐, or tetradentate ligands. The cyanation of aryl bromides is achieved by the copper‐catalyzed in situ production of the corresponding aryl iodides in the presence of catalytic amounts of potassium iodide (see scheme). This protocol involves two main innovations: 1) the use of catalytic amounts of ligands and 2) the use of acetone cyanohydrin as the cyanating agent in copper‐mediated cyanation reactions. Abstract An efficient copper‐catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen‐ and/or oxygen‐binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper‐catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110 °C) compared with the Rosenmund–von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper‐mediated cyanation reactions. An efficient copper-catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen- and/or oxygen-binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper-catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110 degrees C) compared with the Rose nmund-von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper-mediated cyanation reactions. An efficient copper-catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen- and/or oxygen-binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper-catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110 °C) compared with the Rosenmund-von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper-mediated cyanation reactions. An efficient copper-catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen- and/or oxygen-binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper-catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110 degrees C) compared with the Rosenmund-von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper-mediated cyanation reactions. |
| Author | Cristau, Henri-Jean Taillefer, Marc Spindler, Jean-Francis Ouali, Armelle |
| Author_xml | – sequence: 1 givenname: Henri-Jean surname: Cristau fullname: Cristau, Henri-Jean email: cristau@cit.enscm.fr organization: Laboratoire de Chimie Organique, UMR CNRS 5076, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l′Ecole Normale, 34296 Montpellier Cedex 5, France, Fax: (+33) 467-144-319 – sequence: 2 givenname: Armelle surname: Ouali fullname: Ouali, Armelle organization: Laboratoire de Chimie Organique, UMR CNRS 5076, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l′Ecole Normale, 34296 Montpellier Cedex 5, France, Fax: (+33) 467-144-319 – sequence: 3 givenname: Jean-Francis surname: Spindler fullname: Spindler, Jean-Francis organization: Rhodia Organique Fine, Centre de Recherches de Lyon (CRL), 85 avenue des Frères Perret, BP 62, 69192 Saint-Fons Cedex, France – sequence: 4 givenname: Marc surname: Taillefer fullname: Taillefer, Marc email: taillefe@cit.enscm.fr organization: Laboratoire de Chimie Organique, UMR CNRS 5076, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l′Ecole Normale, 34296 Montpellier Cedex 5, France, Fax: (+33) 467-144-319 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/15714537$$D View this record in MEDLINE/PubMed https://hal.science/hal-00384116$$DView record in HAL |
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| Keywords | PALLADIUM acetone cyanohydrin CONVERSION COMPLEXES MICROWAVE IRRADIATION cyanation aryl halides homogeneous catalysis AROMATIC HALIDES NITRILES TRANSITION-METAL CHLORIDES copper N-ARYLATION CYANIDES |
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| PublicationDate | April 8, 2005 |
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| PublicationTitle | Chemistry : a European journal |
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| Snippet | An efficient copper‐catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating... An efficient copper-catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating... Abstract An efficient copper‐catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and... |
| Source | Web of Science |
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| StartPage | 2483 |
| SubjectTerms | acetone cyanohydrin aryl halides Chemical Sciences Chemistry Chemistry, Multidisciplinary copper cyanation homogeneous catalysis Organic chemistry Physical Sciences Science & Technology |
| Title | Mild and Efficient Copper-Catalyzed Cyanation of Aryl Iodides and Bromides |
| URI | https://api.istex.fr/ark:/67375/WNG-5QQ584NK-T/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.200400979 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000228412500022 https://www.ncbi.nlm.nih.gov/pubmed/15714537 https://search.proquest.com/docview/67736703 https://hal.science/hal-00384116 |
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