(π-Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands (DPCB): Highly Active Catalysts for Direct Conversion of Allylic Alcohols
The (π-allyl)palladium complex bearing an sp2-hybridized phosphorus ligand (DPCB-OMe: 1,2-bis(4-methoxyphenyl)-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene) efficiently catalyzes direct conversion of allylic alcohols in the absence of activating agents of alcohols such as Lewis aci...
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| Veröffentlicht in: | Journal of the American Chemical Society 2002-09, Vol.124 (37), p.10968-10969 |
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| container_end_page | 10969 |
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| container_issue | 37 |
| container_start_page | 10968 |
| container_title | Journal of the American Chemical Society |
| container_volume | 124 |
| creator | Ozawa, Fumiyuki Okamoto, Hideyuki Kawagishi, Seiji Yamamoto, Shogo Minami, Tatsuya Yoshifuji, Masaaki |
| description | The (π-allyl)palladium complex bearing an sp2-hybridized phosphorus ligand (DPCB-OMe: 1,2-bis(4-methoxyphenyl)-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene) efficiently catalyzes direct conversion of allylic alcohols in the absence of activating agents of alcohols such as Lewis acids. N-Allylation of aniline proceeds at room temperature to afford monoallylated anilines in 90−97% yields. C-Allylation of active methylene compounds is also successful at 50 °C using a catalytic amount of pyridine as a base, giving monoallylation products in 85−95% yields. The catalytic mechanism involving hydrido- and (π-allyl)palladium intermediates has been proposed on the basis of stoichiometric examinations using model compounds of presumed intermediates. |
| doi_str_mv | 10.1021/ja0274406 |
| format | Article |
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N-Allylation of aniline proceeds at room temperature to afford monoallylated anilines in 90−97% yields. C-Allylation of active methylene compounds is also successful at 50 °C using a catalytic amount of pyridine as a base, giving monoallylation products in 85−95% yields. The catalytic mechanism involving hydrido- and (π-allyl)palladium intermediates has been proposed on the basis of stoichiometric examinations using model compounds of presumed intermediates.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0274406</identifier><identifier>PMID: 12224930</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Kinetics and mechanisms ; Organic chemistry ; Reactivity and mechanisms</subject><ispartof>Journal of the American Chemical Society, 2002-09, Vol.124 (37), p.10968-10969</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-2d9f7a6f2203f5e6340bc0c1f36f0360f3d36201c581d9e91631aec1c607f70a3</citedby><cites>FETCH-LOGICAL-a445t-2d9f7a6f2203f5e6340bc0c1f36f0360f3d36201c581d9e91631aec1c607f70a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja0274406$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0274406$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13920527$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12224930$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ozawa, Fumiyuki</creatorcontrib><creatorcontrib>Okamoto, Hideyuki</creatorcontrib><creatorcontrib>Kawagishi, Seiji</creatorcontrib><creatorcontrib>Yamamoto, Shogo</creatorcontrib><creatorcontrib>Minami, Tatsuya</creatorcontrib><creatorcontrib>Yoshifuji, Masaaki</creatorcontrib><title>(π-Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands (DPCB): Highly Active Catalysts for Direct Conversion of Allylic Alcohols</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>The (π-allyl)palladium complex bearing an sp2-hybridized phosphorus ligand (DPCB-OMe: 1,2-bis(4-methoxyphenyl)-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene) efficiently catalyzes direct conversion of allylic alcohols in the absence of activating agents of alcohols such as Lewis acids. N-Allylation of aniline proceeds at room temperature to afford monoallylated anilines in 90−97% yields. C-Allylation of active methylene compounds is also successful at 50 °C using a catalytic amount of pyridine as a base, giving monoallylation products in 85−95% yields. The catalytic mechanism involving hydrido- and (π-allyl)palladium intermediates has been proposed on the basis of stoichiometric examinations using model compounds of presumed intermediates.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Kinetics and mechanisms</subject><subject>Organic chemistry</subject><subject>Reactivity and mechanisms</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNptkc1u1DAUhS0EokNhwQsgb0CdRcA_iT1hN01bChpEEeVnZ3kce8ZTJw52UjW7bnkAnot34EkwzKizYXXv1f107tG5ADzF6CVGBL_aSER4niN2D0xwQVBWYMLugwlCiGR8xugBeBTjJo05meGH4AATQvKSogn4efTrNps7N7ppJ52TtR0aWPmmc_pGR3isZbDtCp7Ybu1jt7atrXWr1aicXw59auHCrmRbR3h0clEdT1__vv0Bz-1q7UY4V7291rCSvXRj7CM0PiSloFWfTrTXOkTrW-gN_GfAqlSVX3sXH4MHRrqon-zqIfh8dnpZnWeLD2_eVvNFJvO86DNSl4ZLZghB1BSa0RwtFVLYUGYQZcjQmjKCsCpmuC51iRnFUiusGOKGI0kPwYutbhf890HHXjQ2Kp1yaLUfouAE8ZKSPIHTLaiCjzFoI7pgGxlGgZH4-wNx94PEPtuJDstG13tyF3oCnu8AGZV0JshW2bjnaElQQXjisi1nY69v7vYyXAnGKS_E5cUn8XEx-_r-Xf5FfNvrShXFxg-hTdn9x-AfVCurPA</recordid><startdate>20020918</startdate><enddate>20020918</enddate><creator>Ozawa, Fumiyuki</creator><creator>Okamoto, Hideyuki</creator><creator>Kawagishi, Seiji</creator><creator>Yamamoto, Shogo</creator><creator>Minami, Tatsuya</creator><creator>Yoshifuji, Masaaki</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20020918</creationdate><title>(π-Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands (DPCB): Highly Active Catalysts for Direct Conversion of Allylic Alcohols</title><author>Ozawa, Fumiyuki ; Okamoto, Hideyuki ; Kawagishi, Seiji ; Yamamoto, Shogo ; Minami, Tatsuya ; Yoshifuji, Masaaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-2d9f7a6f2203f5e6340bc0c1f36f0360f3d36201c581d9e91631aec1c607f70a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Kinetics and mechanisms</topic><topic>Organic chemistry</topic><topic>Reactivity and mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ozawa, Fumiyuki</creatorcontrib><creatorcontrib>Okamoto, Hideyuki</creatorcontrib><creatorcontrib>Kawagishi, Seiji</creatorcontrib><creatorcontrib>Yamamoto, Shogo</creatorcontrib><creatorcontrib>Minami, Tatsuya</creatorcontrib><creatorcontrib>Yoshifuji, Masaaki</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ozawa, Fumiyuki</au><au>Okamoto, Hideyuki</au><au>Kawagishi, Seiji</au><au>Yamamoto, Shogo</au><au>Minami, Tatsuya</au><au>Yoshifuji, Masaaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(π-Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands (DPCB): Highly Active Catalysts for Direct Conversion of Allylic Alcohols</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2002-09-18</date><risdate>2002</risdate><volume>124</volume><issue>37</issue><spage>10968</spage><epage>10969</epage><pages>10968-10969</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>The (π-allyl)palladium complex bearing an sp2-hybridized phosphorus ligand (DPCB-OMe: 1,2-bis(4-methoxyphenyl)-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene) efficiently catalyzes direct conversion of allylic alcohols in the absence of activating agents of alcohols such as Lewis acids. N-Allylation of aniline proceeds at room temperature to afford monoallylated anilines in 90−97% yields. C-Allylation of active methylene compounds is also successful at 50 °C using a catalytic amount of pyridine as a base, giving monoallylation products in 85−95% yields. The catalytic mechanism involving hydrido- and (π-allyl)palladium intermediates has been proposed on the basis of stoichiometric examinations using model compounds of presumed intermediates.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12224930</pmid><doi>10.1021/ja0274406</doi><tpages>2</tpages></addata></record> |
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| language | eng |
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| source | ACS Publications |
| subjects | Chemistry Exact sciences and technology Kinetics and mechanisms Organic chemistry Reactivity and mechanisms |
| title | (π-Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands (DPCB): Highly Active Catalysts for Direct Conversion of Allylic Alcohols |
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