Copper-Catalyzed N-Arylation of Imidazoles and Benzimidazoles
4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) acce...
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| Veröffentlicht in: | Journal of organic chemistry 2007-08, Vol.72 (16), p.6190-6199 |
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| container_title | Journal of organic chemistry |
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| creator | Altman, Ryan A Koval, Erica D Buchwald, Stephen L |
| description | 4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands. |
| doi_str_mv | 10.1021/jo070807a |
| format | Article |
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Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. 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Org. Chem</addtitle><description>4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands.</description><subject>Benzimidazoles - chemistry</subject><subject>Bromides - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry, Organic - methods</subject><subject>Copper - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Imidazoles - chemistry</subject><subject>Iodides - chemistry</subject><subject>Ligands</subject><subject>Models, Chemical</subject><subject>Organic chemistry</subject><subject>Polyethylene Glycols - chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1Lw0AQhhdRbK0e_AOSi4KH6H4ku5uDhzZYFeoH2oO3ZUxmITVN6m4Ctr_elJb24lwGZh5eXh5Czhm9YZSz21lNFdVUwQHps5jTUCY0OiR9SjkPBZeiR068n9Fu4jg-Jj2mJI-1ln1yl9aLBbowhQbK5Qrz4CUcumUJTVFXQW2Dp3mRw6ou0QdQ5cEIq1WxO52SIwulx7PtHpDp-H6aPoaT14endDgJIYpUE3KtRQKJUsLqPJfI80xLqjhqtCJjAkQkLeMgkVFpRcI5ImRacKQY2VgMyNUmduHqnxZ9Y-aFz7AsocK69UZRFTOmRQdeb8DM1d47tGbhijm4pWHUrFWZnaqOvdiGtl9zzPfk1k0HXG4B8BmU1kGVFX7P6USJSK_bhRuu8A3-7v7gvo1UQsVm-vZhxtN3-jwejc3nPhcy3_VpXdWp-6fgH2NiivQ</recordid><startdate>20070803</startdate><enddate>20070803</enddate><creator>Altman, Ryan A</creator><creator>Koval, Erica D</creator><creator>Buchwald, Stephen L</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20070803</creationdate><title>Copper-Catalyzed N-Arylation of Imidazoles and Benzimidazoles</title><author>Altman, Ryan A ; Koval, Erica D ; Buchwald, Stephen L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-28839a9773f8dd6e2dc86072e8ef3c13a346f12a6e106f3922eeac832e0e4f53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Benzimidazoles - chemistry</topic><topic>Bromides - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chemistry, Organic - methods</topic><topic>Copper - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Imidazoles - chemistry</topic><topic>Iodides - chemistry</topic><topic>Ligands</topic><topic>Models, Chemical</topic><topic>Organic chemistry</topic><topic>Polyethylene Glycols - chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Altman, Ryan A</creatorcontrib><creatorcontrib>Koval, Erica D</creatorcontrib><creatorcontrib>Buchwald, Stephen L</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Altman, Ryan A</au><au>Koval, Erica D</au><au>Buchwald, Stephen L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed N-Arylation of Imidazoles and Benzimidazoles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2007-08-03</date><risdate>2007</risdate><volume>72</volume><issue>16</issue><spage>6190</spage><epage>6199</epage><pages>6190-6199</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17625886</pmid><doi>10.1021/jo070807a</doi><tpages>10</tpages></addata></record> |
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| subjects | Benzimidazoles - chemistry Bromides - chemistry Catalysis Chemistry Chemistry, Organic - methods Copper - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Imidazoles - chemistry Iodides - chemistry Ligands Models, Chemical Organic chemistry Polyethylene Glycols - chemistry Preparations and properties |
| title | Copper-Catalyzed N-Arylation of Imidazoles and Benzimidazoles |
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