HFIP‐Promoted Substitution in the Ferrocene Series: Smooth Approach towards Original Catalysts
Pseudo‐benzylic substitution is an important reaction in the ferrocene series, especially to obtain ligands for catalysis. Herein, we described new reactions conditions, using fluorinated alcohols as both solvent and promoter, able to deliver iodoferrocene derivatives faster than using classical sol...
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| Veröffentlicht in: | European journal of organic chemistry 2021-11, Vol.2021 (41), p.5702-5716 |
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| container_title | European journal of organic chemistry |
| container_volume | 2021 |
| creator | Erb, William Carré, Victor Roisnel, Thierry |
| description | Pseudo‐benzylic substitution is an important reaction in the ferrocene series, especially to obtain ligands for catalysis. Herein, we described new reactions conditions, using fluorinated alcohols as both solvent and promoter, able to deliver iodoferrocene derivatives faster than using classical solvents. Various N, O, P and C‐nucleophiles were found compatible with this transformation which occurs with full retention of stereochemistry. Original P,N‐ligands were prepared by using iodine/lithium exchange‐chlorophoshine trapping sequences, and their properties were evaluated in Suzuki‐Miyaura and Buchwald‐Hartwig coupling as well as in ketone α‐arylation reaction.
Pseudo‐benzylic substitution promoted by fluorinated solvent from various iodoferrocenes is described. These new reaction conditions allow the fast generation of libraries of derivatives for applications in catalysis for example, as demonstrated with the synthesis of original ligands used in cross‐coupling reactions. |
| doi_str_mv | 10.1002/ejoc.202100824 |
| format | Article |
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Pseudo‐benzylic substitution promoted by fluorinated solvent from various iodoferrocenes is described. These new reaction conditions allow the fast generation of libraries of derivatives for applications in catalysis for example, as demonstrated with the synthesis of original ligands used in cross‐coupling reactions.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100824</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alcohols ; Catalysis ; Chemical Sciences ; Cross-coupling ; Ferrocene ; Fluorinated solvent ; Iodine ; Ligand design ; Ligands ; Lithium ; Nucleophiles ; Organic chemistry ; Sequences ; Solvents ; Stereochemistry ; Substitution ; Substitution reactions</subject><ispartof>European journal of organic chemistry, 2021-11, Vol.2021 (41), p.5702-5716</ispartof><rights>2021 Wiley‐VCH GmbH</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-c3914-c85c919b326f30d349abb7a47fd0b4ee34b7ad759a5dd69a044d8b6e63d0d73c3</citedby><cites>FETCH-LOGICAL-c3914-c85c919b326f30d349abb7a47fd0b4ee34b7ad759a5dd69a044d8b6e63d0d73c3</cites><orcidid>0000-0002-6088-4472 ; 0000-0002-2906-2091 ; 0000-0002-4982-6589</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.202100824$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202100824$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03367746$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Erb, William</creatorcontrib><creatorcontrib>Carré, Victor</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><title>HFIP‐Promoted Substitution in the Ferrocene Series: Smooth Approach towards Original Catalysts</title><title>European journal of organic chemistry</title><description>Pseudo‐benzylic substitution is an important reaction in the ferrocene series, especially to obtain ligands for catalysis. Herein, we described new reactions conditions, using fluorinated alcohols as both solvent and promoter, able to deliver iodoferrocene derivatives faster than using classical solvents. Various N, O, P and C‐nucleophiles were found compatible with this transformation which occurs with full retention of stereochemistry. Original P,N‐ligands were prepared by using iodine/lithium exchange‐chlorophoshine trapping sequences, and their properties were evaluated in Suzuki‐Miyaura and Buchwald‐Hartwig coupling as well as in ketone α‐arylation reaction.
Pseudo‐benzylic substitution promoted by fluorinated solvent from various iodoferrocenes is described. These new reaction conditions allow the fast generation of libraries of derivatives for applications in catalysis for example, as demonstrated with the synthesis of original ligands used in cross‐coupling reactions.</description><subject>Alcohols</subject><subject>Catalysis</subject><subject>Chemical Sciences</subject><subject>Cross-coupling</subject><subject>Ferrocene</subject><subject>Fluorinated solvent</subject><subject>Iodine</subject><subject>Ligand design</subject><subject>Ligands</subject><subject>Lithium</subject><subject>Nucleophiles</subject><subject>Organic chemistry</subject><subject>Sequences</subject><subject>Solvents</subject><subject>Stereochemistry</subject><subject>Substitution</subject><subject>Substitution reactions</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkM9LwzAcxYsoOKdXzwFPHjqTJk0Xb6NsbjLYYAreYtqkNqNrZpI6dvNP8G_0L7GjMo-evj_4vMfjBcE1ggMEYXSn1iYfRDBqj2FEToIegoyFkDJ42u4EkxAx_HIeXDi3hhAySlEveJ1OZsvvz6-lNRvjlQSrJnNe-8ZrUwNdA18qMFHWmlzVCqyU1crdg9XGGF-C0XZrjchL4M1OWOnAwuo3XYsKpMKLau-8uwzOClE5dfU7-8HzZPyUTsP54mGWjuZhjhkiYT6Mc4ZYhiNaYCgxYSLLEkGSQsKMKIVJe8kkZiKWkjIBCZHDjCqKJZQJznE_uO18S1HxrdUbYffcCM2nozk__CDGNEkI_UAte9Oxbfr3RjnP16axbWzHo5iROI4QpS016KjcGuesKo62CPJD4_zQOD823gpYJ9jpSu3_ofn4cZH-aX8A-CiF6w</recordid><startdate>20211108</startdate><enddate>20211108</enddate><creator>Erb, William</creator><creator>Carré, Victor</creator><creator>Roisnel, Thierry</creator><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0002-2906-2091</orcidid><orcidid>https://orcid.org/0000-0002-4982-6589</orcidid></search><sort><creationdate>20211108</creationdate><title>HFIP‐Promoted Substitution in the Ferrocene Series: Smooth Approach towards Original Catalysts</title><author>Erb, William ; Carré, Victor ; Roisnel, Thierry</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3914-c85c919b326f30d349abb7a47fd0b4ee34b7ad759a5dd69a044d8b6e63d0d73c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alcohols</topic><topic>Catalysis</topic><topic>Chemical Sciences</topic><topic>Cross-coupling</topic><topic>Ferrocene</topic><topic>Fluorinated solvent</topic><topic>Iodine</topic><topic>Ligand design</topic><topic>Ligands</topic><topic>Lithium</topic><topic>Nucleophiles</topic><topic>Organic chemistry</topic><topic>Sequences</topic><topic>Solvents</topic><topic>Stereochemistry</topic><topic>Substitution</topic><topic>Substitution reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Erb, William</creatorcontrib><creatorcontrib>Carré, Victor</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Erb, William</au><au>Carré, Victor</au><au>Roisnel, Thierry</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>HFIP‐Promoted Substitution in the Ferrocene Series: Smooth Approach towards Original Catalysts</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-11-08</date><risdate>2021</risdate><volume>2021</volume><issue>41</issue><spage>5702</spage><epage>5716</epage><pages>5702-5716</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Pseudo‐benzylic substitution is an important reaction in the ferrocene series, especially to obtain ligands for catalysis. Herein, we described new reactions conditions, using fluorinated alcohols as both solvent and promoter, able to deliver iodoferrocene derivatives faster than using classical solvents. Various N, O, P and C‐nucleophiles were found compatible with this transformation which occurs with full retention of stereochemistry. Original P,N‐ligands were prepared by using iodine/lithium exchange‐chlorophoshine trapping sequences, and their properties were evaluated in Suzuki‐Miyaura and Buchwald‐Hartwig coupling as well as in ketone α‐arylation reaction.
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| language | eng |
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| source | Wiley Journals |
| subjects | Alcohols Catalysis Chemical Sciences Cross-coupling Ferrocene Fluorinated solvent Iodine Ligand design Ligands Lithium Nucleophiles Organic chemistry Sequences Solvents Stereochemistry Substitution Substitution reactions |
| title | HFIP‐Promoted Substitution in the Ferrocene Series: Smooth Approach towards Original Catalysts |
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