Synthesis of difluoromethylated diarylmethanes via Fe(OTf) 3 -catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates
The Fe(OTf) -catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates with electron-rich (hetero)arenes afforded difluoromethylated diarylmethanes. Control experiments showed that Fe(OTf) behaves as the Lewis acid, and that the phosphate leaving group and o- or p-alkoxy substituents...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2021-04, Vol.57 (32), p.3877-3880 |
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container_title | Chemical communications (Cambridge, England) |
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creator | Yamamoto, Yoshihiko Takase, Tomoya Kuroyanagi, Eisuke Yasui, Takeshi |
description | The Fe(OTf)
-catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates with electron-rich (hetero)arenes afforded difluoromethylated diarylmethanes. Control experiments showed that Fe(OTf)
behaves as the Lewis acid, and that the phosphate leaving group and o- or p-alkoxy substituents on the substrates are necessary for the Fe(OTf)
-catalyzed reaction to proceed under mild conditions. |
doi_str_mv | 10.1039/d1cc00765c |
format | Article |
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-catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates with electron-rich (hetero)arenes afforded difluoromethylated diarylmethanes. Control experiments showed that Fe(OTf)
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-catalyzed reaction to proceed under mild conditions.</description><subject>Aromatic compounds</subject><subject>Friedel-Crafts reaction</subject><subject>Lewis acid</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Phosphates</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkU1LxDAQhoMofl_8AVLwsorRpEma5ijVVUHYgwreSjaZsJXuZk1aYf0B_m7T9eNgLhOGh2dmeBE6ouSCEqYuLTWGEFkIs4F2KSs4Frx82Rz-QmHJuNhBezG-kvSoKLfRDmOlpILxXfT5uFp0M4hNzLzLbOPa3gc_h262anUHNrV0WLVDQy8gZu-NzsYwmjy504xl2OhOt6uPxI1DAxZaXAXtupgF0KZr_GKw5uc5_jVjigff2p8tZz4uZ2lMPEBbTrcRDn_qPnoe3zxVd_hhcntfXT1gw4TocO6KEkrj8oIrN1VTsFZxpq0EUgIIYomdCkU46BIkKRSVRIHISa6VlcQVbB-Nvr3L4N96iF09b6KBtk3H-T7WuaCCSCEUS-jJP_TV92GRthsozgRXkiTq7JsywccYwNXL0MzTiTUl9ZBOfU2rap1OleDjH2U_nYP9Q3_jYF-Z3Yr7</recordid><startdate>20210425</startdate><enddate>20210425</enddate><creator>Yamamoto, Yoshihiko</creator><creator>Takase, Tomoya</creator><creator>Kuroyanagi, Eisuke</creator><creator>Yasui, Takeshi</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/0000-0001-8544-6324</orcidid><orcidid>https://orcid.org/0000-0002-7630-8736</orcidid></search><sort><creationdate>20210425</creationdate><title>Synthesis of difluoromethylated diarylmethanes via Fe(OTf) 3 -catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates</title><author>Yamamoto, Yoshihiko ; Takase, Tomoya ; Kuroyanagi, Eisuke ; Yasui, Takeshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-2f68e8cf2649fb9bedd943ad7e08ee50d0db5904ea8e70691709e5202a9d70f63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aromatic compounds</topic><topic>Friedel-Crafts reaction</topic><topic>Lewis acid</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Phosphates</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamamoto, Yoshihiko</creatorcontrib><creatorcontrib>Takase, Tomoya</creatorcontrib><creatorcontrib>Kuroyanagi, Eisuke</creatorcontrib><creatorcontrib>Yasui, Takeshi</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>Yamamoto, Yoshihiko</au><au>Takase, Tomoya</au><au>Kuroyanagi, Eisuke</au><au>Yasui, Takeshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of difluoromethylated diarylmethanes via Fe(OTf) 3 -catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2021-04-25</date><risdate>2021</risdate><volume>57</volume><issue>32</issue><spage>3877</spage><epage>3880</epage><pages>3877-3880</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The Fe(OTf)
-catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates with electron-rich (hetero)arenes afforded difluoromethylated diarylmethanes. Control experiments showed that Fe(OTf)
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-catalyzed reaction to proceed under mild conditions.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>33871534</pmid><doi>10.1039/d1cc00765c</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-8544-6324</orcidid><orcidid>https://orcid.org/0000-0002-7630-8736</orcidid><oa>free_for_read</oa></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Aromatic compounds Friedel-Crafts reaction Lewis acid NMR Nuclear magnetic resonance Phosphates Substrates |
title | Synthesis of difluoromethylated diarylmethanes via Fe(OTf) 3 -catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates |
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