The molecular-level effect of alkoxide additives in iron-catalyzed Kumada cross-coupling with simple ferric salts
The molecular-level role of alkoxide salts, used as alternative additive to N -methylpyrrolidone in iron-catalyzed alkyl-alkenyl/aryl cross-coupling reactions, is investigated. Detailed spectroscopic studies reveal that alkoxides promote the formation of homoleptic organoferrates such as [FeMe 3 ] −...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2023-01, Vol.59 (1), p.1317-132 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Bakas, Nikki J Chourreu, Pablo Gayon, Eric Lefèvre, Guillaume Neidig, Michael L |
| description | The molecular-level role of alkoxide salts, used as alternative additive to
N
-methylpyrrolidone in iron-catalyzed alkyl-alkenyl/aryl cross-coupling reactions, is investigated. Detailed spectroscopic studies reveal that alkoxides promote the formation of homoleptic organoferrates such as [FeMe
3
]
−
, providing an alternative to toxic NMP to access these reactive intermediates.
Alkoxide additives promote the formation of low-coordinate homoleptic iron(
ii
) intermediates in cross-coupling reactions with simple iron salts. |
| doi_str_mv | 10.1039/d2cc06257g |
| format | Article |
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N
-methylpyrrolidone in iron-catalyzed alkyl-alkenyl/aryl cross-coupling reactions, is investigated. Detailed spectroscopic studies reveal that alkoxides promote the formation of homoleptic organoferrates such as [FeMe
3
]
−
, providing an alternative to toxic NMP to access these reactive intermediates.
Alkoxide additives promote the formation of low-coordinate homoleptic iron(
ii
) intermediates in cross-coupling reactions with simple iron salts.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d2cc06257g</identifier><identifier>PMID: 36637039</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Additives ; Alkoxides ; Chemical reactions ; Chemical Sciences ; Coupling (molecular) ; Cross coupling ; Ferric salts ; Iron</subject><ispartof>Chemical communications (Cambridge, England), 2023-01, Vol.59 (1), p.1317-132</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c427t-cc66f332faec5e8a89f8969c7d139038e1c5fe9aca550bb56c662dee517b0bb83</citedby><cites>FETCH-LOGICAL-c427t-cc66f332faec5e8a89f8969c7d139038e1c5fe9aca550bb56c662dee517b0bb83</cites><orcidid>0000-0002-2300-3867 ; 0000-0001-9409-5861</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36637039$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-04293143$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Bakas, Nikki J</creatorcontrib><creatorcontrib>Chourreu, Pablo</creatorcontrib><creatorcontrib>Gayon, Eric</creatorcontrib><creatorcontrib>Lefèvre, Guillaume</creatorcontrib><creatorcontrib>Neidig, Michael L</creatorcontrib><title>The molecular-level effect of alkoxide additives in iron-catalyzed Kumada cross-coupling with simple ferric salts</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The molecular-level role of alkoxide salts, used as alternative additive to
N
-methylpyrrolidone in iron-catalyzed alkyl-alkenyl/aryl cross-coupling reactions, is investigated. Detailed spectroscopic studies reveal that alkoxides promote the formation of homoleptic organoferrates such as [FeMe
3
]
−
, providing an alternative to toxic NMP to access these reactive intermediates.
Alkoxide additives promote the formation of low-coordinate homoleptic iron(
ii
) intermediates in cross-coupling reactions with simple iron salts.</description><subject>Additives</subject><subject>Alkoxides</subject><subject>Chemical reactions</subject><subject>Chemical Sciences</subject><subject>Coupling (molecular)</subject><subject>Cross coupling</subject><subject>Ferric salts</subject><subject>Iron</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkstPGzEQxi1EBZT2wr3IUk9F2taP9T5OFUp5VI3UC5V6sxx7nBi862DvBuhfj0NoKPXFHs9vPmvmM0JHlHymhLdfDNOaVEzU8x10QHlVFqJsfu-uz6Ital6KffQ2pWuSFxXNHtrnVcXrXHqAbq8WgLvgQY9excLDCjwGa0EPOFis_E24dwawMsYNbgUJux67GPpCq0H5hz9g8I-xU0ZhHUNKhQ7j0rt-ju_csMDJdUsP2EKMTuOk_JDeoTdW-QTvn_dD9Ov87GpyWUx_XnyfnE4LXbJ6KLSuKss5swq0gEY1rW3aqtW1obwlvAGqhYVWaSUEmc1ElXlmAAStZzlu-CH6utFdjrMOjIZ-iMrLZXSdig8yKCdfZ3q3kPOwkpQQzvIEs8KnjcLiv7rL06lc35GStZyWfEUz-_H5tRhuR0iDvA5j7HODktU1JYJRTjJ1sqGeZhXBbmUpkWsv5Tc2mTx5eZHh438b2KJ_zcvAhw0Qk95mXz4DfwQh0qXn</recordid><startdate>20230131</startdate><enddate>20230131</enddate><creator>Bakas, Nikki J</creator><creator>Chourreu, Pablo</creator><creator>Gayon, Eric</creator><creator>Lefèvre, Guillaume</creator><creator>Neidig, Michael L</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>1XC</scope><scope>VOOES</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-2300-3867</orcidid><orcidid>https://orcid.org/0000-0001-9409-5861</orcidid></search><sort><creationdate>20230131</creationdate><title>The molecular-level effect of alkoxide additives in iron-catalyzed Kumada cross-coupling with simple ferric salts</title><author>Bakas, Nikki J ; Chourreu, Pablo ; Gayon, Eric ; Lefèvre, Guillaume ; Neidig, Michael L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c427t-cc66f332faec5e8a89f8969c7d139038e1c5fe9aca550bb56c662dee517b0bb83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Additives</topic><topic>Alkoxides</topic><topic>Chemical reactions</topic><topic>Chemical Sciences</topic><topic>Coupling (molecular)</topic><topic>Cross coupling</topic><topic>Ferric salts</topic><topic>Iron</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bakas, Nikki J</creatorcontrib><creatorcontrib>Chourreu, Pablo</creatorcontrib><creatorcontrib>Gayon, Eric</creatorcontrib><creatorcontrib>Lefèvre, Guillaume</creatorcontrib><creatorcontrib>Neidig, Michael L</creatorcontrib><collection>PubMed</collection><collection>CrossRef</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><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bakas, Nikki J</au><au>Chourreu, Pablo</au><au>Gayon, Eric</au><au>Lefèvre, Guillaume</au><au>Neidig, Michael L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The molecular-level effect of alkoxide additives in iron-catalyzed Kumada cross-coupling with simple ferric salts</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2023-01-31</date><risdate>2023</risdate><volume>59</volume><issue>1</issue><spage>1317</spage><epage>132</epage><pages>1317-132</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The molecular-level role of alkoxide salts, used as alternative additive to
N
-methylpyrrolidone in iron-catalyzed alkyl-alkenyl/aryl cross-coupling reactions, is investigated. Detailed spectroscopic studies reveal that alkoxides promote the formation of homoleptic organoferrates such as [FeMe
3
]
−
, providing an alternative to toxic NMP to access these reactive intermediates.
Alkoxide additives promote the formation of low-coordinate homoleptic iron(
ii
) intermediates in cross-coupling reactions with simple iron salts.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36637039</pmid><doi>10.1039/d2cc06257g</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-2300-3867</orcidid><orcidid>https://orcid.org/0000-0001-9409-5861</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2023-01, Vol.59 (1), p.1317-132 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_04293143v1 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Additives Alkoxides Chemical reactions Chemical Sciences Coupling (molecular) Cross coupling Ferric salts Iron |
| title | The molecular-level effect of alkoxide additives in iron-catalyzed Kumada cross-coupling with simple ferric salts |
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