A Direct, Regioselective Palladium-Catalyzed Synthesis of N-Substituted Benzimidazoles and Imidazopyridines
Unsymmetric, N‐substituted benzimidazoles and imidazopyridines can be prepared directly from 2‐halonitroarenes and amides through Pd(TFA)2/(R)‐BINAP‐catalyzed cross‐coupling and subsequent reductive aminocyclization. This sequence can be conducted by a one‐pot procedure. The method is versatile and...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2011-01, Vol.2011 (2), p.234-237 |
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| container_issue | 2 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2011 |
| creator | Alonso, Jorge Halland, Nis Nazaré, Marc R'kyek, Omar Urmann, Matthias Lindenschmidt, Andreas |
| description | Unsymmetric, N‐substituted benzimidazoles and imidazopyridines can be prepared directly from 2‐halonitroarenes and amides through Pd(TFA)2/(R)‐BINAP‐catalyzed cross‐coupling and subsequent reductive aminocyclization. This sequence can be conducted by a one‐pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles.
Unsymmetrical, N‐substituted benzimidazoles can be prepared directly from 2‐halonitroarenes and amides through Pd(TFA)2/(R)‐BINAP‐catalyzed cross‐coupling and subsequent reductive aminocyclization.This sequence can be conducted by a one‐pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles. |
| doi_str_mv | 10.1002/ejoc.201001423 |
| format | Article |
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Unsymmetrical, N‐substituted benzimidazoles can be prepared directly from 2‐halonitroarenes and amides through Pd(TFA)2/(R)‐BINAP‐catalyzed cross‐coupling and subsequent reductive aminocyclization.This sequence can be conducted by a one‐pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201001423</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Benzimidazoles ; 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 ; Homogeneous catalysis ; Nitrogen heterocycles ; Organic chemistry ; Palladium ; Preparations and properties ; Regioselectivity</subject><ispartof>European Journal of Organic Chemistry, 2011-01, Vol.2011 (2), p.234-237</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3573-e399c86b44930679509d9a95e2ef22c0a15d6f685c49db1d5cf823bd34dfcbcf3</citedby><cites>FETCH-LOGICAL-c3573-e399c86b44930679509d9a95e2ef22c0a15d6f685c49db1d5cf823bd34dfcbcf3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201001423$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201001423$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,776,780,788,1411,4009,27901,27902,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23729527$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Alonso, Jorge</creatorcontrib><creatorcontrib>Halland, Nis</creatorcontrib><creatorcontrib>Nazaré, Marc</creatorcontrib><creatorcontrib>R'kyek, Omar</creatorcontrib><creatorcontrib>Urmann, Matthias</creatorcontrib><creatorcontrib>Lindenschmidt, Andreas</creatorcontrib><title>A Direct, Regioselective Palladium-Catalyzed Synthesis of N-Substituted Benzimidazoles and Imidazopyridines</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Unsymmetric, N‐substituted benzimidazoles and imidazopyridines can be prepared directly from 2‐halonitroarenes and amides through Pd(TFA)2/(R)‐BINAP‐catalyzed cross‐coupling and subsequent reductive aminocyclization. This sequence can be conducted by a one‐pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles.
Unsymmetrical, N‐substituted benzimidazoles can be prepared directly from 2‐halonitroarenes and amides through Pd(TFA)2/(R)‐BINAP‐catalyzed cross‐coupling and subsequent reductive aminocyclization.This sequence can be conducted by a one‐pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles.</description><subject>Benzimidazoles</subject><subject>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>Homogeneous catalysis</subject><subject>Nitrogen heterocycles</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>Preparations and properties</subject><subject>Regioselectivity</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkEtPwzAQhCMEEqVw5ZwLN1z8yKM-llBKUVseBZWb5dhrMKRJFadA-utJFVRx47Sz2vlmpfG8U4J7BGN6Ae-F6lHcaBJQtud1COYc4Yjj_UYHLECEs5dD78i5d4wxjyLS8T4G_pUtQVXn_iO82sJB1iz2E_x7mWVS2_USJbKSWb0B7c_rvHoDZ51fGH-G5uvUVbZaV83pEvKNXVotN0UGzpe59sftuqpLq20O7tg7MDJzcPI7u97z9fApuUGTu9E4GUyQYmHMEDDOVT9Kg4AzHMU8xFxzyUOgYChVWJJQRybqhyrgOiU6VKZPWapZoI1KlWFdr9fmqrJwrgQjVqVdyrIWBIttVWJbldhV1QBnLbCSTsnMlDJX1u0oymLKQxo3Pt76vmwG9T-pYnh7l_z9gVrWugq-d6wsP0QUszgUi9lIEJ5MJ8niQUzZD-Hfi_g</recordid><startdate>201101</startdate><enddate>201101</enddate><creator>Alonso, Jorge</creator><creator>Halland, Nis</creator><creator>Nazaré, Marc</creator><creator>R'kyek, Omar</creator><creator>Urmann, Matthias</creator><creator>Lindenschmidt, Andreas</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201101</creationdate><title>A Direct, Regioselective Palladium-Catalyzed Synthesis of N-Substituted Benzimidazoles and Imidazopyridines</title><author>Alonso, Jorge ; Halland, Nis ; Nazaré, Marc ; R'kyek, Omar ; Urmann, Matthias ; Lindenschmidt, Andreas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3573-e399c86b44930679509d9a95e2ef22c0a15d6f685c49db1d5cf823bd34dfcbcf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Benzimidazoles</topic><topic>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>Homogeneous catalysis</topic><topic>Nitrogen heterocycles</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>Preparations and properties</topic><topic>Regioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alonso, Jorge</creatorcontrib><creatorcontrib>Halland, Nis</creatorcontrib><creatorcontrib>Nazaré, Marc</creatorcontrib><creatorcontrib>R'kyek, Omar</creatorcontrib><creatorcontrib>Urmann, Matthias</creatorcontrib><creatorcontrib>Lindenschmidt, Andreas</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alonso, Jorge</au><au>Halland, Nis</au><au>Nazaré, Marc</au><au>R'kyek, Omar</au><au>Urmann, Matthias</au><au>Lindenschmidt, Andreas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Direct, Regioselective Palladium-Catalyzed Synthesis of N-Substituted Benzimidazoles and Imidazopyridines</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2011-01</date><risdate>2011</risdate><volume>2011</volume><issue>2</issue><spage>234</spage><epage>237</epage><pages>234-237</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Unsymmetric, N‐substituted benzimidazoles and imidazopyridines can be prepared directly from 2‐halonitroarenes and amides through Pd(TFA)2/(R)‐BINAP‐catalyzed cross‐coupling and subsequent reductive aminocyclization. This sequence can be conducted by a one‐pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles.
Unsymmetrical, N‐substituted benzimidazoles can be prepared directly from 2‐halonitroarenes and amides through Pd(TFA)2/(R)‐BINAP‐catalyzed cross‐coupling and subsequent reductive aminocyclization.This sequence can be conducted by a one‐pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201001423</doi><tpages>4</tpages></addata></record> |
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| ispartof | European Journal of Organic Chemistry, 2011-01, Vol.2011 (2), p.234-237 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Benzimidazoles 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 Homogeneous catalysis Nitrogen heterocycles Organic chemistry Palladium Preparations and properties Regioselectivity |
| title | A Direct, Regioselective Palladium-Catalyzed Synthesis of N-Substituted Benzimidazoles and Imidazopyridines |
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