Efficient carbene transfer reactivity mediated by Fe() complexes supported by bulky alkoxides
Herein we describe the stoichiometric and catalytic carbene-transfer reactivity of iron( ii ) alkoxide complexes with iodonium ylide precursors. Treatment of PhIC(CO 2 Me) 2 with styrene in the presence of catalytic amounts of several different Fe(OR) 2 (THF) 2 precursors results in efficient cyclop...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2024-07, Vol.6 (55), p.733-736 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Kulathungage, Lakshani W Kurup, Sudheer S Browne, Edison A Spalink, Gabriel H Ward, Cassandra L Lord, Richard L Groysman, Stanislav |
| description | Herein we describe the stoichiometric and catalytic carbene-transfer reactivity of iron(
ii
) alkoxide complexes with iodonium ylide precursors. Treatment of PhIC(CO
2
Me)
2
with styrene in the presence of catalytic amounts of several different Fe(OR)
2
(THF)
2
precursors results in efficient cyclopropanation for a variety of styrenes. Computational and reactivity studies suggest a novel remote metallocarbene/vinyl radical intermediate, Fe(OR)
2
(κ
2
-(O&z.dbd6;C(OMe))
2
C), which could be responsible for the reactive nature of the catalyst.
The reaction of Fe(OR)
2
(THF)
2
(OR = bulky alkoxide ligand) with PhIC(CO
2
Me)
2
results in the formation of reactive remote carbene/vinyl radical intermediate that undergoes facile cyclopropanation or dimerization. |
| doi_str_mv | 10.1039/d4cc02108h |
| format | Article |
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ii
) alkoxide complexes with iodonium ylide precursors. Treatment of PhIC(CO
2
Me)
2
with styrene in the presence of catalytic amounts of several different Fe(OR)
2
(THF)
2
precursors results in efficient cyclopropanation for a variety of styrenes. Computational and reactivity studies suggest a novel remote metallocarbene/vinyl radical intermediate, Fe(OR)
2
(κ
2
-(O&z.dbd6;C(OMe))
2
C), which could be responsible for the reactive nature of the catalyst.
The reaction of Fe(OR)
2
(THF)
2
(OR = bulky alkoxide ligand) with PhIC(CO
2
Me)
2
results in the formation of reactive remote carbene/vinyl radical intermediate that undergoes facile cyclopropanation or dimerization.</description><identifier>ISSN: 1359-7345</identifier><identifier>ISSN: 1364-548X</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d4cc02108h</identifier><identifier>PMID: 38896088</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkoxides ; Carbenes ; Effectiveness ; Iron ; Precursors ; Styrenes ; Vinyl radical</subject><ispartof>Chemical communications (Cambridge, England), 2024-07, Vol.6 (55), p.733-736</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c262t-bfd2fa6f950b1491f86da3dd6bf46fd1690737f99b8e50103bb6f990e13c00873</cites><orcidid>0000-0003-3578-7985 ; 0000-0001-6692-0369</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38896088$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kulathungage, Lakshani W</creatorcontrib><creatorcontrib>Kurup, Sudheer S</creatorcontrib><creatorcontrib>Browne, Edison A</creatorcontrib><creatorcontrib>Spalink, Gabriel H</creatorcontrib><creatorcontrib>Ward, Cassandra L</creatorcontrib><creatorcontrib>Lord, Richard L</creatorcontrib><creatorcontrib>Groysman, Stanislav</creatorcontrib><title>Efficient carbene transfer reactivity mediated by Fe() complexes supported by bulky alkoxides</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Herein we describe the stoichiometric and catalytic carbene-transfer reactivity of iron(
ii
) alkoxide complexes with iodonium ylide precursors. Treatment of PhIC(CO
2
Me)
2
with styrene in the presence of catalytic amounts of several different Fe(OR)
2
(THF)
2
precursors results in efficient cyclopropanation for a variety of styrenes. Computational and reactivity studies suggest a novel remote metallocarbene/vinyl radical intermediate, Fe(OR)
2
(κ
2
-(O&z.dbd6;C(OMe))
2
C), which could be responsible for the reactive nature of the catalyst.
The reaction of Fe(OR)
2
(THF)
2
(OR = bulky alkoxide ligand) with PhIC(CO
2
Me)
2
results in the formation of reactive remote carbene/vinyl radical intermediate that undergoes facile cyclopropanation or dimerization.</description><subject>Alkoxides</subject><subject>Carbenes</subject><subject>Effectiveness</subject><subject>Iron</subject><subject>Precursors</subject><subject>Styrenes</subject><subject>Vinyl radical</subject><issn>1359-7345</issn><issn>1364-548X</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpd0UtLxDAUBeAgiu-NeyXgRoXqTdOmyVLGJwhuFNxIyeMGq522Jq04_96OMyqYTQL345CcELLH4JQBV2cusxZSBvJlhWwyLrIkz-TT6vycq6TgWb5BtmJ8hXGxXK6TDS6lEiDlJnm-9L6yFTY9tToYbJD2QTfRY6ABte2rj6qf0Sm6SvfoqJnRKzw6praddjV-YqRx6Lo2LGdmqN9mVNdv7WflMO6QNa_riLvLfZs8Xl0-TG6Su_vr28n5XWJTkfaJ8S71WniVg2GZYl4Kp7lzwvhMeMeEgoIXXikjMYfxzcaMWAEybgFkwbfJ0SK3C-37gLEvp1W0WNe6wXaIJYcCJGSQz-nhP_raDqEZbzdXuUhl8R14slA2tDEG9GUXqqkOs5JBOS-9vMgmk-_Sb0Z8sIwczFjUL_1peQT7CxCi_Z3-_Rr_Agn6hj0</recordid><startdate>20240704</startdate><enddate>20240704</enddate><creator>Kulathungage, Lakshani W</creator><creator>Kurup, Sudheer S</creator><creator>Browne, Edison A</creator><creator>Spalink, Gabriel H</creator><creator>Ward, Cassandra L</creator><creator>Lord, Richard L</creator><creator>Groysman, Stanislav</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>7X8</scope><orcidid>https://orcid.org/0000-0003-3578-7985</orcidid><orcidid>https://orcid.org/0000-0001-6692-0369</orcidid></search><sort><creationdate>20240704</creationdate><title>Efficient carbene transfer reactivity mediated by Fe() complexes supported by bulky alkoxides</title><author>Kulathungage, Lakshani W ; Kurup, Sudheer S ; Browne, Edison A ; Spalink, Gabriel H ; Ward, Cassandra L ; Lord, Richard L ; Groysman, Stanislav</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c262t-bfd2fa6f950b1491f86da3dd6bf46fd1690737f99b8e50103bb6f990e13c00873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkoxides</topic><topic>Carbenes</topic><topic>Effectiveness</topic><topic>Iron</topic><topic>Precursors</topic><topic>Styrenes</topic><topic>Vinyl radical</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kulathungage, Lakshani W</creatorcontrib><creatorcontrib>Kurup, Sudheer S</creatorcontrib><creatorcontrib>Browne, Edison A</creatorcontrib><creatorcontrib>Spalink, Gabriel H</creatorcontrib><creatorcontrib>Ward, Cassandra L</creatorcontrib><creatorcontrib>Lord, Richard L</creatorcontrib><creatorcontrib>Groysman, Stanislav</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>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kulathungage, Lakshani W</au><au>Kurup, Sudheer S</au><au>Browne, Edison A</au><au>Spalink, Gabriel H</au><au>Ward, Cassandra L</au><au>Lord, Richard L</au><au>Groysman, Stanislav</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient carbene transfer reactivity mediated by Fe() complexes supported by bulky alkoxides</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2024-07-04</date><risdate>2024</risdate><volume>6</volume><issue>55</issue><spage>733</spage><epage>736</epage><pages>733-736</pages><issn>1359-7345</issn><issn>1364-548X</issn><eissn>1364-548X</eissn><abstract>Herein we describe the stoichiometric and catalytic carbene-transfer reactivity of iron(
ii
) alkoxide complexes with iodonium ylide precursors. Treatment of PhIC(CO
2
Me)
2
with styrene in the presence of catalytic amounts of several different Fe(OR)
2
(THF)
2
precursors results in efficient cyclopropanation for a variety of styrenes. Computational and reactivity studies suggest a novel remote metallocarbene/vinyl radical intermediate, Fe(OR)
2
(κ
2
-(O&z.dbd6;C(OMe))
2
C), which could be responsible for the reactive nature of the catalyst.
The reaction of Fe(OR)
2
(THF)
2
(OR = bulky alkoxide ligand) with PhIC(CO
2
Me)
2
results in the formation of reactive remote carbene/vinyl radical intermediate that undergoes facile cyclopropanation or dimerization.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38896088</pmid><doi>10.1039/d4cc02108h</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-3578-7985</orcidid><orcidid>https://orcid.org/0000-0001-6692-0369</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2024-07, Vol.6 (55), p.733-736 |
| issn | 1359-7345 1364-548X 1364-548X |
| language | eng |
| recordid | cdi_proquest_journals_3075628787 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Alkoxides Carbenes Effectiveness Iron Precursors Styrenes Vinyl radical |
| title | Efficient carbene transfer reactivity mediated by Fe() complexes supported by bulky alkoxides |
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