Regiodivergent Arylation of Pyridines via Zincke Intermediates

Regiodivergent Arylation of Pyridines via Zincke Intermediates

An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of pyridines with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed arylation at the putative C4 position. Recyclization then prov...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2024-02, Vol.63 (8), p.e202315418-n/a
Hauptverfasser: Wang, Haiwen, Greaney, Michael F.
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
C−H Activation
Intermediates
Palladium
Pyridine
Pyridines
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page n/a
container_issue 8
container_start_page e202315418
container_title Angewandte Chemie International Edition
container_volume 63
creator Wang, Haiwen
Greaney, Michael F.
description An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of pyridines with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed arylation at the putative C4 position. Recyclization then provides the pyridine products. Alternatively, metal‐free arylation with a diaryliodonium salt is selective for the pyridine meta‐position, affording a regiodivergent approach to pyridine biaryls from a common intermediate. Arylation of pyridines is possible through ring‐opened Zincke imines. A Pd‐catalyzed Heck‐type process is selective for the C4 position, while a metal‐free arylation using an iodonium salt addresses the C5‐position. Sequential triflation, arylation, and pyridine recyclization enables the process to be conducted in one pot, representing a new approach to valuable biaryl structures.
doi_str_mv 10.1002/anie.202315418
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2892272344</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2924898518</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4138-f2bc0f08b61abf90e796dbb7b9bc4abb08bff92723679dec7244568753c05ce53</originalsourceid><addsrcrecordid>eNqF0EtLAzEUBeAgiq3VrUsZcONmal4zSTZCKT4KoiK6cROSzB2JTmdqMlX6702pD3DjKoF895B7EDokeEwwpqem9TCmmDJScCK30JAUlORMCLad7pyxXMiCDNBejC_JS4nLXTRgQsnk1RCd3cOz7yr_DuEZ2j6bhFVjet-1WVdnd6vgK99CzN69yZ58614hm7U9hDlU3vQQ99FObZoIB1_nCD1enD9Mr_Lr28vZdHKdO06YzGtqHa6xtCUxtlYYhCora4VV1nFjbXqpa0UFZaVQFThBOS9KKQrmcOGgYCN0ssldhO5tCbHXcx8dNI1poVtGTaWi63HOEz3-Q1-6ZWjT7zRVlMu0OZFJjTfKhS7GALVeBD83YaUJ1utm9bpZ_dNsGjj6il3atP0P_64yAbUBH76B1T9xenIzO_8N_wRozoR8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2924898518</pqid></control><display><type>article</type><title>Regiodivergent Arylation of Pyridines via Zincke Intermediates</title><source>Wiley Journals</source><creator>Wang, Haiwen ; Greaney, Michael F.</creator><creatorcontrib>Wang, Haiwen ; Greaney, Michael F.</creatorcontrib><description>An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of pyridines with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed arylation at the putative C4 position. Recyclization then provides the pyridine products. Alternatively, metal‐free arylation with a diaryliodonium salt is selective for the pyridine meta‐position, affording a regiodivergent approach to pyridine biaryls from a common intermediate. Arylation of pyridines is possible through ring‐opened Zincke imines. A Pd‐catalyzed Heck‐type process is selective for the C4 position, while a metal‐free arylation using an iodonium salt addresses the C5‐position. Sequential triflation, arylation, and pyridine recyclization enables the process to be conducted in one pot, representing a new approach to valuable biaryl structures.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202315418</identifier><identifier>PMID: 37985419</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Catalysis ; C−H Activation ; Intermediates ; Palladium ; Pyridine ; Pyridines</subject><ispartof>Angewandte Chemie International Edition, 2024-02, Vol.63 (8), p.e202315418-n/a</ispartof><rights>2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH</rights><rights>2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.</rights><rights>2023. This article is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4138-f2bc0f08b61abf90e796dbb7b9bc4abb08bff92723679dec7244568753c05ce53</citedby><cites>FETCH-LOGICAL-c4138-f2bc0f08b61abf90e796dbb7b9bc4abb08bff92723679dec7244568753c05ce53</cites><orcidid>0000-0001-9633-1135</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.202315418$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202315418$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37985419$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Haiwen</creatorcontrib><creatorcontrib>Greaney, Michael F.</creatorcontrib><title>Regiodivergent Arylation of Pyridines via Zincke Intermediates</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of pyridines with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed arylation at the putative C4 position. Recyclization then provides the pyridine products. Alternatively, metal‐free arylation with a diaryliodonium salt is selective for the pyridine meta‐position, affording a regiodivergent approach to pyridine biaryls from a common intermediate. Arylation of pyridines is possible through ring‐opened Zincke imines. A Pd‐catalyzed Heck‐type process is selective for the C4 position, while a metal‐free arylation using an iodonium salt addresses the C5‐position. Sequential triflation, arylation, and pyridine recyclization enables the process to be conducted in one pot, representing a new approach to valuable biaryl structures.</description><subject>Catalysis</subject><subject>C−H Activation</subject><subject>Intermediates</subject><subject>Palladium</subject><subject>Pyridine</subject><subject>Pyridines</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqF0EtLAzEUBeAgiq3VrUsZcONmal4zSTZCKT4KoiK6cROSzB2JTmdqMlX6702pD3DjKoF895B7EDokeEwwpqem9TCmmDJScCK30JAUlORMCLad7pyxXMiCDNBejC_JS4nLXTRgQsnk1RCd3cOz7yr_DuEZ2j6bhFVjet-1WVdnd6vgK99CzN69yZ58614hm7U9hDlU3vQQ99FObZoIB1_nCD1enD9Mr_Lr28vZdHKdO06YzGtqHa6xtCUxtlYYhCora4VV1nFjbXqpa0UFZaVQFThBOS9KKQrmcOGgYCN0ssldhO5tCbHXcx8dNI1poVtGTaWi63HOEz3-Q1-6ZWjT7zRVlMu0OZFJjTfKhS7GALVeBD83YaUJ1utm9bpZ_dNsGjj6il3atP0P_64yAbUBH76B1T9xenIzO_8N_wRozoR8</recordid><startdate>20240219</startdate><enddate>20240219</enddate><creator>Wang, Haiwen</creator><creator>Greaney, Michael F.</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9633-1135</orcidid></search><sort><creationdate>20240219</creationdate><title>Regiodivergent Arylation of Pyridines via Zincke Intermediates</title><author>Wang, Haiwen ; Greaney, Michael F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4138-f2bc0f08b61abf90e796dbb7b9bc4abb08bff92723679dec7244568753c05ce53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Catalysis</topic><topic>C−H Activation</topic><topic>Intermediates</topic><topic>Palladium</topic><topic>Pyridine</topic><topic>Pyridines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Haiwen</creatorcontrib><creatorcontrib>Greaney, Michael F.</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health &amp; 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>Wang, Haiwen</au><au>Greaney, Michael F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regiodivergent Arylation of Pyridines via Zincke Intermediates</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2024-02-19</date><risdate>2024</risdate><volume>63</volume><issue>8</issue><spage>e202315418</spage><epage>n/a</epage><pages>e202315418-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of pyridines with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed arylation at the putative C4 position. Recyclization then provides the pyridine products. Alternatively, metal‐free arylation with a diaryliodonium salt is selective for the pyridine meta‐position, affording a regiodivergent approach to pyridine biaryls from a common intermediate. Arylation of pyridines is possible through ring‐opened Zincke imines. A Pd‐catalyzed Heck‐type process is selective for the C4 position, while a metal‐free arylation using an iodonium salt addresses the C5‐position. Sequential triflation, arylation, and pyridine recyclization enables the process to be conducted in one pot, representing a new approach to valuable biaryl structures.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>37985419</pmid><doi>10.1002/anie.202315418</doi><tpages>4</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-9633-1135</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie International Edition, 2024-02, Vol.63 (8), p.e202315418-n/a
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_2892272344
source Wiley Journals
subjects Catalysis
C−H Activation
Intermediates
Palladium
Pyridine
Pyridines
title Regiodivergent Arylation of Pyridines via Zincke Intermediates
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T14%3A28%3A01IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Regiodivergent%20Arylation%20of%20Pyridines%20via%20Zincke%20Intermediates&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Wang,%20Haiwen&rft.date=2024-02-19&rft.volume=63&rft.issue=8&rft.spage=e202315418&rft.epage=n/a&rft.pages=e202315418-n/a&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.202315418&rft_dat=%3Cproquest_cross%3E2924898518%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2924898518&rft_id=info:pmid/37985419&rfr_iscdi=true