Synthesis of Complexes with Abnormal "Protic" N-Heterocyclic Carbenes
Neutral 4‐iodo‐N‐ethylimidazole 3 oxidatively adds to [Pt(PPh3)4] to give, in the presence of different tetraalkylammonium salts, complexes trans‐[4], trans‐[5], and trans‐[6] containing an anionic C4‐bound heterocycle with an unsubstituted ring‐nitrogen atom. Complex trans‐[4] reacts with the proto...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-11, Vol.54 (46), p.13811-13815 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Jin, Hanpeng Tan, Tristan Tsai Yuan Hahn, F. Ekkehardt |
| description | Neutral 4‐iodo‐N‐ethylimidazole 3 oxidatively adds to [Pt(PPh3)4] to give, in the presence of different tetraalkylammonium salts, complexes trans‐[4], trans‐[5], and trans‐[6] containing an anionic C4‐bound heterocycle with an unsubstituted ring‐nitrogen atom. Complex trans‐[4] reacts with the proton source NH4I under protonation of the ring‐nitrogen atom to produce complex trans‐[7]I which bears an NH,NR‐substituted aNHC ligand. The reaction of trans‐[4] with CH3I yields the complex trans‐[8]I which has a classical aNHC ligand with two alkylated ring‐nitrogen atoms.
The oxidative addition of neutral 4‐iodo‐N‐ethylimidazole to [Pt(PPh3)4] yields the complex trans‐[1] bearing an anionic C4‐bound heterocycle. Complex trans‐[1] can be N3‐protonated and N3‐methylated giving complexes with protic and conventional aNHC ligands, respectively. (aNHC=abnormal N‐heterocyclic carbene; NHC=N‐heterocyclic carbene). |
| doi_str_mv | 10.1002/anie.201507206 |
| format | Article |
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The oxidative addition of neutral 4‐iodo‐N‐ethylimidazole to [Pt(PPh3)4] yields the complex trans‐[1] bearing an anionic C4‐bound heterocycle. Complex trans‐[1] can be N3‐protonated and N3‐methylated giving complexes with protic and conventional aNHC ligands, respectively. (aNHC=abnormal N‐heterocyclic carbene; NHC=N‐heterocyclic carbene).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201507206</identifier><identifier>PMID: 26403225</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkylation ; Carbenes ; Ligands ; N-heterocyclic carbenes ; oxidative addition ; platinum ; Protonation ; Synthesis (chemistry)</subject><ispartof>Angewandte Chemie International Edition, 2015-11, Vol.54 (46), p.13811-13815</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5216-bf14ea4621ffe766aace6827e86ff37508c57f2f8111e32699b77274725f06433</citedby><cites>FETCH-LOGICAL-c5216-bf14ea4621ffe766aace6827e86ff37508c57f2f8111e32699b77274725f06433</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%2Fanie.201507206$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201507206$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26403225$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jin, Hanpeng</creatorcontrib><creatorcontrib>Tan, Tristan Tsai Yuan</creatorcontrib><creatorcontrib>Hahn, F. Ekkehardt</creatorcontrib><title>Synthesis of Complexes with Abnormal "Protic" N-Heterocyclic Carbenes</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Neutral 4‐iodo‐N‐ethylimidazole 3 oxidatively adds to [Pt(PPh3)4] to give, in the presence of different tetraalkylammonium salts, complexes trans‐[4], trans‐[5], and trans‐[6] containing an anionic C4‐bound heterocycle with an unsubstituted ring‐nitrogen atom. Complex trans‐[4] reacts with the proton source NH4I under protonation of the ring‐nitrogen atom to produce complex trans‐[7]I which bears an NH,NR‐substituted aNHC ligand. The reaction of trans‐[4] with CH3I yields the complex trans‐[8]I which has a classical aNHC ligand with two alkylated ring‐nitrogen atoms.
The oxidative addition of neutral 4‐iodo‐N‐ethylimidazole to [Pt(PPh3)4] yields the complex trans‐[1] bearing an anionic C4‐bound heterocycle. Complex trans‐[1] can be N3‐protonated and N3‐methylated giving complexes with protic and conventional aNHC ligands, respectively. (aNHC=abnormal N‐heterocyclic carbene; NHC=N‐heterocyclic carbene).</description><subject>Alkylation</subject><subject>Carbenes</subject><subject>Ligands</subject><subject>N-heterocyclic carbenes</subject><subject>oxidative addition</subject><subject>platinum</subject><subject>Protonation</subject><subject>Synthesis (chemistry)</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqNkTtvGzEQhIkght9tyuDgNG5O4eOOS5WColgGDCV-ISXBY5YwnbujQp5g69-btmwhSJNU3OKbWe4MIR8YHTFK-WfTexxxymoKnMp3ZJ_VnJUCQLzPcyVECapme-QgpfvMK0XlLtnjsqKC83qfzK7X_XCHyaciuGIaumWLj5iKBz_cFZOmD7EzbXHyPYbB25NiUc5xwBjs2rbeFlMTG-wxHZEdZ9qEx6_vIbn9OruZzsuLb2fn08lFafOvZNk4VqGpJGfOIUhpjEWpOKCSzgmoqbI1OO4UYwwFl-NxA8ChAl47KvMxh-R047uM4fcK06A7nyy2rekxrJJmAFTkJCr1H6jIeVA-5hn99Bd6H1axz4dkiitgQF92jzaUjSGliE4vo-9MXGtG9XMX-rkLve0iCz6-2q6aDn9u8bfwMzDeAA--xfU_7PRkcT7707zcaH0a8HGrNfGXlpCj1D8WZ3oBdF5fXn3RUjwBAZWhLw</recordid><startdate>20151109</startdate><enddate>20151109</enddate><creator>Jin, Hanpeng</creator><creator>Tan, Tristan Tsai Yuan</creator><creator>Hahn, F. Ekkehardt</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20151109</creationdate><title>Synthesis of Complexes with Abnormal "Protic" N-Heterocyclic Carbenes</title><author>Jin, Hanpeng ; Tan, Tristan Tsai Yuan ; Hahn, F. Ekkehardt</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5216-bf14ea4621ffe766aace6827e86ff37508c57f2f8111e32699b77274725f06433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkylation</topic><topic>Carbenes</topic><topic>Ligands</topic><topic>N-heterocyclic carbenes</topic><topic>oxidative addition</topic><topic>platinum</topic><topic>Protonation</topic><topic>Synthesis (chemistry)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jin, Hanpeng</creatorcontrib><creatorcontrib>Tan, Tristan Tsai Yuan</creatorcontrib><creatorcontrib>Hahn, F. Ekkehardt</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jin, Hanpeng</au><au>Tan, Tristan Tsai Yuan</au><au>Hahn, F. Ekkehardt</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Complexes with Abnormal "Protic" N-Heterocyclic Carbenes</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-11-09</date><risdate>2015</risdate><volume>54</volume><issue>46</issue><spage>13811</spage><epage>13815</epage><pages>13811-13815</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Neutral 4‐iodo‐N‐ethylimidazole 3 oxidatively adds to [Pt(PPh3)4] to give, in the presence of different tetraalkylammonium salts, complexes trans‐[4], trans‐[5], and trans‐[6] containing an anionic C4‐bound heterocycle with an unsubstituted ring‐nitrogen atom. Complex trans‐[4] reacts with the proton source NH4I under protonation of the ring‐nitrogen atom to produce complex trans‐[7]I which bears an NH,NR‐substituted aNHC ligand. The reaction of trans‐[4] with CH3I yields the complex trans‐[8]I which has a classical aNHC ligand with two alkylated ring‐nitrogen atoms.
The oxidative addition of neutral 4‐iodo‐N‐ethylimidazole to [Pt(PPh3)4] yields the complex trans‐[1] bearing an anionic C4‐bound heterocycle. Complex trans‐[1] can be N3‐protonated and N3‐methylated giving complexes with protic and conventional aNHC ligands, respectively. (aNHC=abnormal N‐heterocyclic carbene; NHC=N‐heterocyclic carbene).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26403225</pmid><doi>10.1002/anie.201507206</doi><tpages>5</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkylation Carbenes Ligands N-heterocyclic carbenes oxidative addition platinum Protonation Synthesis (chemistry) |
| title | Synthesis of Complexes with Abnormal "Protic" N-Heterocyclic Carbenes |
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