Pd/Cu‐Catalyzed Defluorinative Carbonylative Coupling of Aryl Iodides and gem‐Difluoroalkenes: Efficient Synthesis of α‐Fluorochalcones
An unprecedented and challenging defluorinative carbonylation was achieved. Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem‐difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible a...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2021-04, Vol.60 (16), p.8818-8822 |
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| creator | Wu, Fu‐Peng Yuan, Yang Liu, Jiawang Wu, Xiao‐Feng |
| description | An unprecedented and challenging defluorinative carbonylation was achieved. Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem‐difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α‐fluorochalcones under mild reaction conditions in moderate‐to‐excellent yields. Mechanistic studies indicated transmetalation between palladium and copper intermediates as a crucial step of the catalytic cycle.
Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem‐difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α‐fluorochalcones under mild reaction conditions in moderate‐to‐excellent yields. |
| doi_str_mv | 10.1002/anie.202017365 |
| format | Article |
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Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem‐difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α‐fluorochalcones under mild reaction conditions in moderate‐to‐excellent yields.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202017365</identifier><identifier>PMID: 33538042</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aromatic compounds ; carbonylation ; Carbonyls ; Catalysts ; Copper ; Coupling ; coupling reactions ; Intermediates ; Iodides ; Palladium ; Substrates ; α-fluorochalcones</subject><ispartof>Angewandte Chemie International Edition, 2021-04, Vol.60 (16), p.8818-8822</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>2021 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3735-5281da85f26bd3d1e101e4a4d4435d2e437a5f9984169619e3f8d1ecb27c60733</citedby><cites>FETCH-LOGICAL-c3735-5281da85f26bd3d1e101e4a4d4435d2e437a5f9984169619e3f8d1ecb27c60733</cites><orcidid>0000-0001-6622-3328</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%2Fanie.202017365$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202017365$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33538042$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Fu‐Peng</creatorcontrib><creatorcontrib>Yuan, Yang</creatorcontrib><creatorcontrib>Liu, Jiawang</creatorcontrib><creatorcontrib>Wu, Xiao‐Feng</creatorcontrib><title>Pd/Cu‐Catalyzed Defluorinative Carbonylative Coupling of Aryl Iodides and gem‐Difluoroalkenes: Efficient Synthesis of α‐Fluorochalcones</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>An unprecedented and challenging defluorinative carbonylation was achieved. Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem‐difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α‐fluorochalcones under mild reaction conditions in moderate‐to‐excellent yields. Mechanistic studies indicated transmetalation between palladium and copper intermediates as a crucial step of the catalytic cycle.
Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem‐difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α‐fluorochalcones under mild reaction conditions in moderate‐to‐excellent yields.</description><subject>Aromatic compounds</subject><subject>carbonylation</subject><subject>Carbonyls</subject><subject>Catalysts</subject><subject>Copper</subject><subject>Coupling</subject><subject>coupling reactions</subject><subject>Intermediates</subject><subject>Iodides</subject><subject>Palladium</subject><subject>Substrates</subject><subject>α-fluorochalcones</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqF0U9u1DAYBfAIUdFS2LJEkdiwydT_47AbpVM6UlWQgLXliT-3Lh57iBNQWHECxFW4SA_BSfB0hiKxYWVb-r0nS68onmE0wwiREx0czAgiCNdU8AfFEeYEV7Su6cN8Z5RWteT4sHic0k32UiLxqDiklFOJGDkqvr81J-3469uPVg_aT1_BlKdg_Rh7F_TgPkPZ6n4Vw-T3rzhuvAtXZbTlvJ98uYzGGUilDqa8gnVuOnV3-aj9RwiQXpULa13nIAzluykM15Bc2sZvf2Z8dke7a-27mPGT4sBqn-Dp_jwuPpwt3rfn1cWb18t2flF1tKa84kRioyW3RKwMNRgwwsA0M4xRbggwWmtum0YyLBqBG6BWZtWtSN0JVFN6XLzc9W76-GmENKi1Sx14rwPEMSnCpGCiJoJk-uIfehPHPuTfKcJRQwgjXGQ126mujyn1YNWmd2vdTwojtV1KbZdS90vlwPN97bhag7nnf6bJoNmBL87D9J86Nb9cLv6W_wa0aaR7</recordid><startdate>20210412</startdate><enddate>20210412</enddate><creator>Wu, Fu‐Peng</creator><creator>Yuan, Yang</creator><creator>Liu, Jiawang</creator><creator>Wu, Xiao‐Feng</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6622-3328</orcidid></search><sort><creationdate>20210412</creationdate><title>Pd/Cu‐Catalyzed Defluorinative Carbonylative Coupling of Aryl Iodides and gem‐Difluoroalkenes: Efficient Synthesis of α‐Fluorochalcones</title><author>Wu, Fu‐Peng ; Yuan, Yang ; Liu, Jiawang ; Wu, Xiao‐Feng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3735-5281da85f26bd3d1e101e4a4d4435d2e437a5f9984169619e3f8d1ecb27c60733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aromatic compounds</topic><topic>carbonylation</topic><topic>Carbonyls</topic><topic>Catalysts</topic><topic>Copper</topic><topic>Coupling</topic><topic>coupling reactions</topic><topic>Intermediates</topic><topic>Iodides</topic><topic>Palladium</topic><topic>Substrates</topic><topic>α-fluorochalcones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Fu‐Peng</creatorcontrib><creatorcontrib>Yuan, Yang</creatorcontrib><creatorcontrib>Liu, Jiawang</creatorcontrib><creatorcontrib>Wu, Xiao‐Feng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Fu‐Peng</au><au>Yuan, Yang</au><au>Liu, Jiawang</au><au>Wu, Xiao‐Feng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pd/Cu‐Catalyzed Defluorinative Carbonylative Coupling of Aryl Iodides and gem‐Difluoroalkenes: Efficient Synthesis of α‐Fluorochalcones</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2021-04-12</date><risdate>2021</risdate><volume>60</volume><issue>16</issue><spage>8818</spage><epage>8822</epage><pages>8818-8822</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>An unprecedented and challenging defluorinative carbonylation was achieved. Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem‐difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α‐fluorochalcones under mild reaction conditions in moderate‐to‐excellent yields. Mechanistic studies indicated transmetalation between palladium and copper intermediates as a crucial step of the catalytic cycle.
Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem‐difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α‐fluorochalcones under mild reaction conditions in moderate‐to‐excellent yields.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>33538042</pmid><doi>10.1002/anie.202017365</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-6622-3328</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aromatic compounds carbonylation Carbonyls Catalysts Copper Coupling coupling reactions Intermediates Iodides Palladium Substrates α-fluorochalcones |
| title | Pd/Cu‐Catalyzed Defluorinative Carbonylative Coupling of Aryl Iodides and gem‐Difluoroalkenes: Efficient Synthesis of α‐Fluorochalcones |
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