The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling
The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the performance of the pre-catalyst is inversely proportional t...
Gespeichert in:
| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2016-01, Vol.45 (40), p.15811-15817 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 15817 |
|---|---|
| container_issue | 40 |
| container_start_page | 15811 |
| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 45 |
| creator | Bedford, Robin B Brenner, Peter B Elorriaga, David Harvey, Jeremy N Nunn, Joshua |
| description | The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover. |
| doi_str_mv | 10.1039/c6dt01823h |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1845831104</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1845831104</sourcerecordid><originalsourceid>FETCH-LOGICAL-c356t-373f983cfd9d8de2c355dbc89d896c4f5e3ccf4f720d589f31e831ab14eeaba93</originalsourceid><addsrcrecordid>eNqNkEtPwzAQhC0EoqVw4QcgHxFSwPY6Dx9ReRRRiUuRuEWuvW6DHKfEyaH_ntAWzpx2Z_TtSDuEXHJ2yxmoO5PZjvFCwPqIjLnM80QJkMd_u8hG5CzGT8aEYKk4JSORA6hBjsnHYo20Cs73GAzSxtFuMHy10sFSs0avO6ToHJqONoFWbRMSXVcBE6M77bcRLX3ta201NW0TY2KafuOrsDonJ077iBeHOSHvT4-L6SyZvz2_TO_niYE06xLIwakCjLPKFhbF4KZ2aYpBqcxIlyIY46TLBbNpoRxwLIDrJZeIeqkVTMj1PnfTNl89xq6sq2jQex2w6WPJC5kOF5zJf6AiyxlIgAG92aO7p1p05aatat1uS87Kn9LLafaw2JU-G-CrQ26_rNH-ob8twzd0Bnz_</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1826703433</pqid></control><display><type>article</type><title>The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Bedford, Robin B ; Brenner, Peter B ; Elorriaga, David ; Harvey, Jeremy N ; Nunn, Joshua</creator><creatorcontrib>Bedford, Robin B ; Brenner, Peter B ; Elorriaga, David ; Harvey, Jeremy N ; Nunn, Joshua</creatorcontrib><description>The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c6dt01823h</identifier><identifier>PMID: 27339002</identifier><language>eng</language><publisher>England</publisher><subject>Amines ; Bromides ; Chelates ; Chelating ; Cross coupling ; Iron ; Ligands ; Magnesium chloride</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2016-01, Vol.45 (40), p.15811-15817</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-373f983cfd9d8de2c355dbc89d896c4f5e3ccf4f720d589f31e831ab14eeaba93</citedby><cites>FETCH-LOGICAL-c356t-373f983cfd9d8de2c355dbc89d896c4f5e3ccf4f720d589f31e831ab14eeaba93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27339002$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bedford, Robin B</creatorcontrib><creatorcontrib>Brenner, Peter B</creatorcontrib><creatorcontrib>Elorriaga, David</creatorcontrib><creatorcontrib>Harvey, Jeremy N</creatorcontrib><creatorcontrib>Nunn, Joshua</creatorcontrib><title>The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover.</description><subject>Amines</subject><subject>Bromides</subject><subject>Chelates</subject><subject>Chelating</subject><subject>Cross coupling</subject><subject>Iron</subject><subject>Ligands</subject><subject>Magnesium chloride</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqNkEtPwzAQhC0EoqVw4QcgHxFSwPY6Dx9ReRRRiUuRuEWuvW6DHKfEyaH_ntAWzpx2Z_TtSDuEXHJ2yxmoO5PZjvFCwPqIjLnM80QJkMd_u8hG5CzGT8aEYKk4JSORA6hBjsnHYo20Cs73GAzSxtFuMHy10sFSs0avO6ToHJqONoFWbRMSXVcBE6M77bcRLX3ta201NW0TY2KafuOrsDonJ077iBeHOSHvT4-L6SyZvz2_TO_niYE06xLIwakCjLPKFhbF4KZ2aYpBqcxIlyIY46TLBbNpoRxwLIDrJZeIeqkVTMj1PnfTNl89xq6sq2jQex2w6WPJC5kOF5zJf6AiyxlIgAG92aO7p1p05aatat1uS87Kn9LLafaw2JU-G-CrQ26_rNH-ob8twzd0Bnz_</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Bedford, Robin B</creator><creator>Brenner, Peter B</creator><creator>Elorriaga, David</creator><creator>Harvey, Jeremy N</creator><creator>Nunn, Joshua</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20160101</creationdate><title>The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling</title><author>Bedford, Robin B ; Brenner, Peter B ; Elorriaga, David ; Harvey, Jeremy N ; Nunn, Joshua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-373f983cfd9d8de2c355dbc89d896c4f5e3ccf4f720d589f31e831ab14eeaba93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Amines</topic><topic>Bromides</topic><topic>Chelates</topic><topic>Chelating</topic><topic>Cross coupling</topic><topic>Iron</topic><topic>Ligands</topic><topic>Magnesium chloride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bedford, Robin B</creatorcontrib><creatorcontrib>Brenner, Peter B</creatorcontrib><creatorcontrib>Elorriaga, David</creatorcontrib><creatorcontrib>Harvey, Jeremy N</creatorcontrib><creatorcontrib>Nunn, Joshua</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bedford, Robin B</au><au>Brenner, Peter B</au><au>Elorriaga, David</au><au>Harvey, Jeremy N</au><au>Nunn, Joshua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2016-01-01</date><risdate>2016</risdate><volume>45</volume><issue>40</issue><spage>15811</spage><epage>15817</epage><pages>15811-15817</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>The application of a variety of iron complexes with chelating amine ligands as pre-catalysts in the representative cross-coupling of 4-tolylmagnesium bromide with cyclohexyl bromide was investigated. The results from this study indicate the performance of the pre-catalyst is inversely proportional to the strength of the chelate or macrocyclic effect of the amine ligand, as determined by the propensity of the ligand to be displaced from the iron centre by reaction with excess benzyl magnesium chloride. The findings from this study are consistent with a catalytic cycle wherein the chelating amine ligand is not coordinated to the iron centre during turnover.</abstract><cop>England</cop><pmid>27339002</pmid><doi>10.1039/c6dt01823h</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2016-01, Vol.45 (40), p.15811-15817 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1845831104 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amines Bromides Chelates Chelating Cross coupling Iron Ligands Magnesium chloride |
| title | The influence of the ligand chelate effect on iron-amine-catalysed Kumada cross-coupling |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-21T08%3A45%3A23IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=The%20influence%20of%20the%20ligand%20chelate%20effect%20on%20iron-amine-catalysed%20Kumada%20cross-coupling&rft.jtitle=Dalton%20transactions%20:%20an%20international%20journal%20of%20inorganic%20chemistry&rft.au=Bedford,%20Robin%20B&rft.date=2016-01-01&rft.volume=45&rft.issue=40&rft.spage=15811&rft.epage=15817&rft.pages=15811-15817&rft.issn=1477-9226&rft.eissn=1477-9234&rft_id=info:doi/10.1039/c6dt01823h&rft_dat=%3Cproquest_cross%3E1845831104%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1826703433&rft_id=info:pmid/27339002&rfr_iscdi=true |