Deuterium-Labeling Studies on the C–H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe3)4
Abstract Deuterium-labeling experiments were performed for the Fe(PMe 3 ) 4 -catalyzed C–H/olefin coupling using a deuterium-labeled aromatic ketone with various alkenes. While the reactions with a variety of alkenes provided the linear alkylation products formed via 1,2-insertion of alkene into an...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2021-09, Vol.53 (18), p.3383-3389 |
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| container_title | Synthesis (Stuttgart) |
| container_volume | 53 |
| creator | Kimura, Naoki Katta, Shiori Kitazawa, Yoichi Kochi, Takuya Kakiuchi, Fumitoshi |
| description | Abstract
Deuterium-labeling experiments were performed for the Fe(PMe
3
)
4
-catalyzed C–H/olefin coupling using a deuterium-labeled aromatic ketone with various alkenes. While the reactions with a variety of alkenes provided the linear alkylation products formed via 1,2-insertion of alkene into an Fe–H bond, the reversible 2,1-insertion proceeded during the reaction highly depends on the choice of the alkene. No H/D scrambling resulting from 2,1-insertion/β-elimination was detected for the reactions with a vinylsilane and
N
-vinylcarbazole, but the reactions with styrenes are considered to involve rapid 2,1-insertion/ β-elimination processes to cause significant levels of H/D scrambling. |
| doi_str_mv | 10.1055/s-0040-1706040 |
| format | Article |
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Deuterium-labeling experiments were performed for the Fe(PMe
3
)
4
-catalyzed C–H/olefin coupling using a deuterium-labeled aromatic ketone with various alkenes. While the reactions with a variety of alkenes provided the linear alkylation products formed via 1,2-insertion of alkene into an Fe–H bond, the reversible 2,1-insertion proceeded during the reaction highly depends on the choice of the alkene. No H/D scrambling resulting from 2,1-insertion/β-elimination was detected for the reactions with a vinylsilane and
N
-vinylcarbazole, but the reactions with styrenes are considered to involve rapid 2,1-insertion/ β-elimination processes to cause significant levels of H/D scrambling.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0040-1706040</identifier><language>eng</language><publisher>Rüdigerstraße 14, 70469 Stuttgart, Germany: Georg Thieme Verlag KG</publisher><subject>special topic</subject><ispartof>Synthesis (Stuttgart), 2021-09, Vol.53 (18), p.3383-3389</ispartof><rights>Thieme. All rights reserved</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2580-8b1576984e3d4fd6a5186f198f5b528fc0b012b5482d31356654f92acda7d9c93</citedby><cites>FETCH-LOGICAL-c2580-8b1576984e3d4fd6a5186f198f5b528fc0b012b5482d31356654f92acda7d9c93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1706040.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0040-1706040$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3004,3005,27901,27902,54534,54535</link.rule.ids></links><search><creatorcontrib>Kimura, Naoki</creatorcontrib><creatorcontrib>Katta, Shiori</creatorcontrib><creatorcontrib>Kitazawa, Yoichi</creatorcontrib><creatorcontrib>Kochi, Takuya</creatorcontrib><creatorcontrib>Kakiuchi, Fumitoshi</creatorcontrib><title>Deuterium-Labeling Studies on the C–H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe3)4</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
Deuterium-labeling experiments were performed for the Fe(PMe
3
)
4
-catalyzed C–H/olefin coupling using a deuterium-labeled aromatic ketone with various alkenes. While the reactions with a variety of alkenes provided the linear alkylation products formed via 1,2-insertion of alkene into an Fe–H bond, the reversible 2,1-insertion proceeded during the reaction highly depends on the choice of the alkene. No H/D scrambling resulting from 2,1-insertion/β-elimination was detected for the reactions with a vinylsilane and
N
-vinylcarbazole, but the reactions with styrenes are considered to involve rapid 2,1-insertion/ β-elimination processes to cause significant levels of H/D scrambling.</description><subject>special topic</subject><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp1kLFOwzAURS0EEqWwMnuEwe1zHCfOWAVKEUVFAiS2yImfaaokRnEylIl_4A_5ElLaleku91xdHUIuOUw4SDn1DCAExmOIhjwiIx6KmAUc3o7JCEAkLFaKn5Iz7zcAEAciGZH8BvsO27Kv2VLnWJXNO33uelOip66h3Rpp-vP1vZiuKrRlQ1PXf_yVnKWz1tW6Kwv6gJ1rBiDVna62n2hovqVzvHp6RHEdnpMTqyuPF4cck9f57Uu6YMvV3X06W7IikAqYyrmMo0SFKExoTaQlV5HlibIyl4GyBeTAg1yGKjCCCxlFMrRJoAujY5MUiRiTyX63aJ33Ldrsoy1r3W4zDtnOUOaznaHsYGgA2B7o1iXWmG1c3zbDw__6vxEMZk4</recordid><startdate>20210916</startdate><enddate>20210916</enddate><creator>Kimura, Naoki</creator><creator>Katta, Shiori</creator><creator>Kitazawa, Yoichi</creator><creator>Kochi, Takuya</creator><creator>Kakiuchi, Fumitoshi</creator><general>Georg Thieme Verlag KG</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20210916</creationdate><title>Deuterium-Labeling Studies on the C–H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe3)4</title><author>Kimura, Naoki ; Katta, Shiori ; Kitazawa, Yoichi ; Kochi, Takuya ; Kakiuchi, Fumitoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2580-8b1576984e3d4fd6a5186f198f5b528fc0b012b5482d31356654f92acda7d9c93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>special topic</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kimura, Naoki</creatorcontrib><creatorcontrib>Katta, Shiori</creatorcontrib><creatorcontrib>Kitazawa, Yoichi</creatorcontrib><creatorcontrib>Kochi, Takuya</creatorcontrib><creatorcontrib>Kakiuchi, Fumitoshi</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kimura, Naoki</au><au>Katta, Shiori</au><au>Kitazawa, Yoichi</au><au>Kochi, Takuya</au><au>Kakiuchi, Fumitoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Deuterium-Labeling Studies on the C–H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe3)4</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2021-09-16</date><risdate>2021</risdate><volume>53</volume><issue>18</issue><spage>3383</spage><epage>3389</epage><pages>3383-3389</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
Deuterium-labeling experiments were performed for the Fe(PMe
3
)
4
-catalyzed C–H/olefin coupling using a deuterium-labeled aromatic ketone with various alkenes. While the reactions with a variety of alkenes provided the linear alkylation products formed via 1,2-insertion of alkene into an Fe–H bond, the reversible 2,1-insertion proceeded during the reaction highly depends on the choice of the alkene. No H/D scrambling resulting from 2,1-insertion/β-elimination was detected for the reactions with a vinylsilane and
N
-vinylcarbazole, but the reactions with styrenes are considered to involve rapid 2,1-insertion/ β-elimination processes to cause significant levels of H/D scrambling.</abstract><cop>Rüdigerstraße 14, 70469 Stuttgart, Germany</cop><pub>Georg Thieme Verlag KG</pub><doi>10.1055/s-0040-1706040</doi><tpages>7</tpages></addata></record> |
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| language | eng |
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| source | Thieme Connect Journals |
| subjects | special topic |
| title | Deuterium-Labeling Studies on the C–H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe3)4 |
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