Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding
A Friedel–Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1‐diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the CF bond through hydrogen bonding is p...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-12, Vol.53 (50), p.13835-13839 |
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| container_issue | 50 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Champagne, Pier Alexandre Benhassine, Yasmine Desroches, Justine Paquin, Jean-François |
| description | A Friedel–Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1‐diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the CF bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups.
Be selective! A Friedel–Crafts benzylation of arenes with benzyl fluorides (see example; HFIP=1,1,1,3,3,3‐hexafluoro‐2‐propanol) is proposed to proceed by a mechanism involving activation of the CF bond through hydrogen bonding. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups. |
| doi_str_mv | 10.1002/anie.201406088 |
| format | Article |
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Be selective! A Friedel–Crafts benzylation of arenes with benzyl fluorides (see example; HFIP=1,1,1,3,3,3‐hexafluoro‐2‐propanol) is proposed to proceed by a mechanism involving activation of the CF bond through hydrogen bonding. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201406088</identifier><identifier>PMID: 25303636</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation ; Alkanes ; arenes ; Aromatic compounds ; benzyl fluorides ; CF activation ; Fluorides ; Friedel-Crafts reaction ; Hydrogen bonding ; hydrogen bonds ; Lewis acid ; Transition metals</subject><ispartof>Angewandte Chemie International Edition, 2014-12, Vol.53 (50), p.13835-13839</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5198-9efcf33f1eeb632f582ab5d568e65c0bf795f88bec1b42174971235449b5fbe13</citedby><cites>FETCH-LOGICAL-c5198-9efcf33f1eeb632f582ab5d568e65c0bf795f88bec1b42174971235449b5fbe13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201406088$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201406088$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25303636$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Champagne, Pier Alexandre</creatorcontrib><creatorcontrib>Benhassine, Yasmine</creatorcontrib><creatorcontrib>Desroches, Justine</creatorcontrib><creatorcontrib>Paquin, Jean-François</creatorcontrib><title>Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A Friedel–Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1‐diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the CF bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups.
Be selective! A Friedel–Crafts benzylation of arenes with benzyl fluorides (see example; HFIP=1,1,1,3,3,3‐hexafluoro‐2‐propanol) is proposed to proceed by a mechanism involving activation of the CF bond through hydrogen bonding. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups.</description><subject>Activation</subject><subject>Alkanes</subject><subject>arenes</subject><subject>Aromatic compounds</subject><subject>benzyl fluorides</subject><subject>CF activation</subject><subject>Fluorides</subject><subject>Friedel-Crafts reaction</subject><subject>Hydrogen bonding</subject><subject>hydrogen bonds</subject><subject>Lewis acid</subject><subject>Transition metals</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkctuEzEUhi0EoqWwZYm8ZDPBl_Fl2KVR0hZVRUq5SGwse-a4MjjjYifQ6evwIDwSr8CEtBG7rv4jne__Nj9CLymZUELYG9sHmDBCayKJ1o_QIRWMVlwp_ni8a84rpQU9QM9K-TryWhP5FB0wwQmXXB6itMgBOojVLFu_LngJtl2H1OPk8TH0t0PEi7hJOXRQ3uJLiDC-fwCebsPek7M_v34v8HHqu4JtwfPeuggddgM-HbqcrqD_9wz91XP0xNtY4MVdHqGPi_mH2Wl1_v7kbDY9r1pBG1014FvPuacATnLmhWbWiU5IDVK0xHnVCK-1g5a6mlFVN4oyLuq6ccI7oPwIvd55r3P6voGyNqtQWojR9pA2xVBFSNMQNrYeRCWvmWy0kiM62aFtTqVk8OY6h5XNg6HEbPcw2z3Mfo-x8OrOvXEr6Pb4_QAj0OyAnyHC8IDOTC_O5v_Lq103lDXc7Ls2fzNScSXM54sT8-nLZb3k75aG8r96VKbl</recordid><startdate>20141208</startdate><enddate>20141208</enddate><creator>Champagne, Pier Alexandre</creator><creator>Benhassine, Yasmine</creator><creator>Desroches, Justine</creator><creator>Paquin, Jean-François</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20141208</creationdate><title>Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding</title><author>Champagne, Pier Alexandre ; Benhassine, Yasmine ; Desroches, Justine ; Paquin, Jean-François</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5198-9efcf33f1eeb632f582ab5d568e65c0bf795f88bec1b42174971235449b5fbe13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Activation</topic><topic>Alkanes</topic><topic>arenes</topic><topic>Aromatic compounds</topic><topic>benzyl fluorides</topic><topic>CF activation</topic><topic>Fluorides</topic><topic>Friedel-Crafts reaction</topic><topic>Hydrogen bonding</topic><topic>hydrogen bonds</topic><topic>Lewis acid</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Champagne, Pier Alexandre</creatorcontrib><creatorcontrib>Benhassine, Yasmine</creatorcontrib><creatorcontrib>Desroches, Justine</creatorcontrib><creatorcontrib>Paquin, Jean-François</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Champagne, Pier Alexandre</au><au>Benhassine, Yasmine</au><au>Desroches, Justine</au><au>Paquin, Jean-François</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-12-08</date><risdate>2014</risdate><volume>53</volume><issue>50</issue><spage>13835</spage><epage>13839</epage><pages>13835-13839</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A Friedel–Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1‐diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the CF bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups.
Be selective! A Friedel–Crafts benzylation of arenes with benzyl fluorides (see example; HFIP=1,1,1,3,3,3‐hexafluoro‐2‐propanol) is proposed to proceed by a mechanism involving activation of the CF bond through hydrogen bonding. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25303636</pmid><doi>10.1002/anie.201406088</doi><tpages>5</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library All Journals |
| subjects | Activation Alkanes arenes Aromatic compounds benzyl fluorides CF activation Fluorides Friedel-Crafts reaction Hydrogen bonding hydrogen bonds Lewis acid Transition metals |
| title | Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding |
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