Nickel-Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar-M (M=MgX, ZnX)
A new method for the regioselective three component cross‐coupling reaction of alkyl halides, 1,3‐butadienes, and aryl‐Grignard reagents has been developed by the use of a nickel catalyst. This reaction proceeds efficiently at 25 °C using (dppf)NiCl2 as a catalyst. Alkyl chlorides, bromides, and iod...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2004-07, Vol.346 (8), p.905-908 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 908 |
|---|---|
| container_issue | 8 |
| container_start_page | 905 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 346 |
| creator | Terao, Jun Nii, Shinsuke Chowdhury, Firoz A. Nakamura, Akifumi Kambe, Nobuaki |
| description | A new method for the regioselective three component cross‐coupling reaction of alkyl halides, 1,3‐butadienes, and aryl‐Grignard reagents has been developed by the use of a nickel catalyst. This reaction proceeds efficiently at 25 °C using (dppf)NiCl2 as a catalyst. Alkyl chlorides, bromides, and iodides can be used as suitable alkylating reagents. The reaction also proceeds when arylzinc halides are used instead of Grignard reagents. Competitive reactions of a mixture of primary, secondary, and tertiary alkyl bromides showed that the reactivities of the halides increase in the order primary |
| doi_str_mv | 10.1002/adsc.200404041 |
| format | Article |
| fullrecord | <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_adsc_200404041</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ADSC200404041</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3911-6a175c00d7c634f8ccc3c45ebbed8bab9e86335aaf9ed2ad9b3680cddaae8c343</originalsourceid><addsrcrecordid>eNqFkE1PwkAURRujiYhuXc9SE4szTD8XLrBqMQJGRCVuJq8zrzgytKRTVPz1QjDEnXmLexfnvMV1nGNGW4zS9jkoK1ttSr31sR2nwQLmux4L4t1t9-m-c2DtO6UsjMKw4SwGWk7RuAnUYJbfqMgQJ7q0aFDW-gPJ6K1CJEk5m5cFFvWqLeZGF5MVByuiLEiZk46ZLg3pgtEK7Rm5XNSgNBbrDoUincrtk5P-RX8yPiOvxfj00NnLwVg8-s2m83RzPUq6bu8-vU06PVfymDE3ABb6klIVyoB7eSSl5NLzMctQRRlkMUYB5z5AHqNqg4ozHkRUKgWAkeQebzqtzV9ZldZWmIt5pWdQLQWjYj2aWI8mtqOthHgjfGqDy39o0bl6TP667sbVtsavrQvVVAQhD33xMkiFnz48x3fpUET8Bzv4gPo</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Nickel-Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar-M (M=MgX, ZnX)</title><source>Access via Wiley Online Library</source><creator>Terao, Jun ; Nii, Shinsuke ; Chowdhury, Firoz A. ; Nakamura, Akifumi ; Kambe, Nobuaki</creator><creatorcontrib>Terao, Jun ; Nii, Shinsuke ; Chowdhury, Firoz A. ; Nakamura, Akifumi ; Kambe, Nobuaki</creatorcontrib><description>A new method for the regioselective three component cross‐coupling reaction of alkyl halides, 1,3‐butadienes, and aryl‐Grignard reagents has been developed by the use of a nickel catalyst. This reaction proceeds efficiently at 25 °C using (dppf)NiCl2 as a catalyst. Alkyl chlorides, bromides, and iodides can be used as suitable alkylating reagents. The reaction also proceeds when arylzinc halides are used instead of Grignard reagents. Competitive reactions of a mixture of primary, secondary, and tertiary alkyl bromides showed that the reactivities of the halides increase in the order primary<secondary<tertiary. A possible reaction pathway involving single electron transfer from a nickelate complex to alkyl halides is proposed.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.200404041</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>alkyl halides ; butadiene ; cross-coupling ; CC bond formation ; Grignard reagents ; multicomponent reactions ; nickel</subject><ispartof>Advanced synthesis & catalysis, 2004-07, Vol.346 (8), p.905-908</ispartof><rights>Copyright © 2004 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3911-6a175c00d7c634f8ccc3c45ebbed8bab9e86335aaf9ed2ad9b3680cddaae8c343</citedby><cites>FETCH-LOGICAL-c3911-6a175c00d7c634f8ccc3c45ebbed8bab9e86335aaf9ed2ad9b3680cddaae8c343</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%2Fadsc.200404041$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.200404041$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27928,27929,45578,45579</link.rule.ids></links><search><creatorcontrib>Terao, Jun</creatorcontrib><creatorcontrib>Nii, Shinsuke</creatorcontrib><creatorcontrib>Chowdhury, Firoz A.</creatorcontrib><creatorcontrib>Nakamura, Akifumi</creatorcontrib><creatorcontrib>Kambe, Nobuaki</creatorcontrib><title>Nickel-Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar-M (M=MgX, ZnX)</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>A new method for the regioselective three component cross‐coupling reaction of alkyl halides, 1,3‐butadienes, and aryl‐Grignard reagents has been developed by the use of a nickel catalyst. This reaction proceeds efficiently at 25 °C using (dppf)NiCl2 as a catalyst. Alkyl chlorides, bromides, and iodides can be used as suitable alkylating reagents. The reaction also proceeds when arylzinc halides are used instead of Grignard reagents. Competitive reactions of a mixture of primary, secondary, and tertiary alkyl bromides showed that the reactivities of the halides increase in the order primary<secondary<tertiary. A possible reaction pathway involving single electron transfer from a nickelate complex to alkyl halides is proposed.</description><subject>alkyl halides</subject><subject>butadiene</subject><subject>cross-coupling</subject><subject>CC bond formation</subject><subject>Grignard reagents</subject><subject>multicomponent reactions</subject><subject>nickel</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkE1PwkAURRujiYhuXc9SE4szTD8XLrBqMQJGRCVuJq8zrzgytKRTVPz1QjDEnXmLexfnvMV1nGNGW4zS9jkoK1ttSr31sR2nwQLmux4L4t1t9-m-c2DtO6UsjMKw4SwGWk7RuAnUYJbfqMgQJ7q0aFDW-gPJ6K1CJEk5m5cFFvWqLeZGF5MVByuiLEiZk46ZLg3pgtEK7Rm5XNSgNBbrDoUincrtk5P-RX8yPiOvxfj00NnLwVg8-s2m83RzPUq6bu8-vU06PVfymDE3ABb6klIVyoB7eSSl5NLzMctQRRlkMUYB5z5AHqNqg4ozHkRUKgWAkeQebzqtzV9ZldZWmIt5pWdQLQWjYj2aWI8mtqOthHgjfGqDy39o0bl6TP667sbVtsavrQvVVAQhD33xMkiFnz48x3fpUET8Bzv4gPo</recordid><startdate>200407</startdate><enddate>200407</enddate><creator>Terao, Jun</creator><creator>Nii, Shinsuke</creator><creator>Chowdhury, Firoz A.</creator><creator>Nakamura, Akifumi</creator><creator>Kambe, Nobuaki</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200407</creationdate><title>Nickel-Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar-M (M=MgX, ZnX)</title><author>Terao, Jun ; Nii, Shinsuke ; Chowdhury, Firoz A. ; Nakamura, Akifumi ; Kambe, Nobuaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3911-6a175c00d7c634f8ccc3c45ebbed8bab9e86335aaf9ed2ad9b3680cddaae8c343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>alkyl halides</topic><topic>butadiene</topic><topic>cross-coupling</topic><topic>CC bond formation</topic><topic>Grignard reagents</topic><topic>multicomponent reactions</topic><topic>nickel</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Terao, Jun</creatorcontrib><creatorcontrib>Nii, Shinsuke</creatorcontrib><creatorcontrib>Chowdhury, Firoz A.</creatorcontrib><creatorcontrib>Nakamura, Akifumi</creatorcontrib><creatorcontrib>Kambe, Nobuaki</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Terao, Jun</au><au>Nii, Shinsuke</au><au>Chowdhury, Firoz A.</au><au>Nakamura, Akifumi</au><au>Kambe, Nobuaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nickel-Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar-M (M=MgX, ZnX)</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2004-07</date><risdate>2004</risdate><volume>346</volume><issue>8</issue><spage>905</spage><epage>908</epage><pages>905-908</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A new method for the regioselective three component cross‐coupling reaction of alkyl halides, 1,3‐butadienes, and aryl‐Grignard reagents has been developed by the use of a nickel catalyst. This reaction proceeds efficiently at 25 °C using (dppf)NiCl2 as a catalyst. Alkyl chlorides, bromides, and iodides can be used as suitable alkylating reagents. The reaction also proceeds when arylzinc halides are used instead of Grignard reagents. Competitive reactions of a mixture of primary, secondary, and tertiary alkyl bromides showed that the reactivities of the halides increase in the order primary<secondary<tertiary. A possible reaction pathway involving single electron transfer from a nickelate complex to alkyl halides is proposed.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.200404041</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2004-07, Vol.346 (8), p.905-908 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_adsc_200404041 |
| source | Access via Wiley Online Library |
| subjects | alkyl halides butadiene cross-coupling CC bond formation Grignard reagents multicomponent reactions nickel |
| title | Nickel-Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar-M (M=MgX, ZnX) |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-16T22%3A38%3A52IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Nickel-Catalyzed%20Regioselective%20Three%20Component%20Coupling%20Reaction%20of%20Alkyl%20Halides,%20Butadienes,%20and%20Ar-M%20(M=MgX,%20ZnX)&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Terao,%20Jun&rft.date=2004-07&rft.volume=346&rft.issue=8&rft.spage=905&rft.epage=908&rft.pages=905-908&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.200404041&rft_dat=%3Cwiley_cross%3EADSC200404041%3C/wiley_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |