Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides
A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under o...
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society 2018-12, Vol.140 (51), p.17878-17883 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 17883 |
|---|---|
| container_issue | 51 |
| container_start_page | 17878 |
| container_title | Journal of the American Chemical Society |
| container_volume | 140 |
| creator | Derosa, Joseph Kleinmans, Roman Tran, Van T Karunananda, Malkanthi K Wisniewski, Steven R Eastgate, Martin D Engle, Keary M |
| description | A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amine are compatible substrates. This method represents the first example of regiocontrolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on the potential substrate binding mode and the role of the EDO ligand in the reductive elimination step. |
| doi_str_mv | 10.1021/jacs.8b11942 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2237503322</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2237503322</sourcerecordid><originalsourceid>FETCH-LOGICAL-a357t-1a79902163ff1b8a19c58fffb4df8fa86d5916c62103b303b7d6d3592f0cba393</originalsourceid><addsrcrecordid>eNqFkDtPwzAURi0EoqWwMaOMDE3xtWPHHqvylCoYgDly_JDSOkmJk6H8ely1wILEcPXpSsef7YPQJeAZYAI3K6XDTJQAMiNHaAyM4JQB4cdojDEmaS44HaGzEFZxzYiAUzSimBHGcjZG8rnSa-vTheqV335ak8CUpLeV6rZe9VXbJK1LXqt6420y92vbbH0yrytjwzk6ccoHe3HICXq_v3tbPKbLl4enxXyZKsryPgWVSxnfyalzUAoFUjPhnCsz44RTghsmgWtOANOSxskNN5RJ4rAuFZV0gq73vZuu_Rhs6Iu6Ctp6rxrbDqEghOYMUxrzXxQYg4wJSSM63aO6a0PorCs2XVXHXxeAi53XYue1OHiN-NWheShra37gb5G_V-9Ordqha6KTv7u-ALI2fjE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2155145893</pqid></control><display><type>article</type><title>Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides</title><source>ACS Publications</source><source>MEDLINE</source><creator>Derosa, Joseph ; Kleinmans, Roman ; Tran, Van T ; Karunananda, Malkanthi K ; Wisniewski, Steven R ; Eastgate, Martin D ; Engle, Keary M</creator><creatorcontrib>Derosa, Joseph ; Kleinmans, Roman ; Tran, Van T ; Karunananda, Malkanthi K ; Wisniewski, Steven R ; Eastgate, Martin D ; Engle, Keary M</creatorcontrib><description>A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amine are compatible substrates. This method represents the first example of regiocontrolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on the potential substrate binding mode and the role of the EDO ligand in the reductive elimination step.</description><identifier>ISSN: 0002-7863</identifier><identifier>ISSN: 1520-5126</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.8b11942</identifier><identifier>PMID: 30525575</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkenes - chemical synthesis ; amides ; Amides - chemical synthesis ; Boronic Acids - chemistry ; Catalysis ; Coordination Complexes - chemistry ; cross-coupling reactions ; dimethyl fumarate ; Dimethyl Fumarate - chemistry ; esters ; Iodobenzenes - chemistry ; Ligands ; Models, Chemical ; moieties ; Nickel - chemistry ; olefin ; organoiodine compounds</subject><ispartof>Journal of the American Chemical Society, 2018-12, Vol.140 (51), p.17878-17883</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a357t-1a79902163ff1b8a19c58fffb4df8fa86d5916c62103b303b7d6d3592f0cba393</citedby><cites>FETCH-LOGICAL-a357t-1a79902163ff1b8a19c58fffb4df8fa86d5916c62103b303b7d6d3592f0cba393</cites><orcidid>0000-0001-6035-4394 ; 0000-0003-2767-6556 ; 0000-0002-6487-3121 ; 0000-0002-8697-8864 ; 0000-0001-8672-4875</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jacs.8b11942$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.8b11942$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30525575$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Derosa, Joseph</creatorcontrib><creatorcontrib>Kleinmans, Roman</creatorcontrib><creatorcontrib>Tran, Van T</creatorcontrib><creatorcontrib>Karunananda, Malkanthi K</creatorcontrib><creatorcontrib>Wisniewski, Steven R</creatorcontrib><creatorcontrib>Eastgate, Martin D</creatorcontrib><creatorcontrib>Engle, Keary M</creatorcontrib><title>Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amine are compatible substrates. This method represents the first example of regiocontrolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on the potential substrate binding mode and the role of the EDO ligand in the reductive elimination step.</description><subject>Alkenes - chemical synthesis</subject><subject>amides</subject><subject>Amides - chemical synthesis</subject><subject>Boronic Acids - chemistry</subject><subject>Catalysis</subject><subject>Coordination Complexes - chemistry</subject><subject>cross-coupling reactions</subject><subject>dimethyl fumarate</subject><subject>Dimethyl Fumarate - chemistry</subject><subject>esters</subject><subject>Iodobenzenes - chemistry</subject><subject>Ligands</subject><subject>Models, Chemical</subject><subject>moieties</subject><subject>Nickel - chemistry</subject><subject>olefin</subject><subject>organoiodine compounds</subject><issn>0002-7863</issn><issn>1520-5126</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkDtPwzAURi0EoqWwMaOMDE3xtWPHHqvylCoYgDly_JDSOkmJk6H8ely1wILEcPXpSsef7YPQJeAZYAI3K6XDTJQAMiNHaAyM4JQB4cdojDEmaS44HaGzEFZxzYiAUzSimBHGcjZG8rnSa-vTheqV335ak8CUpLeV6rZe9VXbJK1LXqt6420y92vbbH0yrytjwzk6ccoHe3HICXq_v3tbPKbLl4enxXyZKsryPgWVSxnfyalzUAoFUjPhnCsz44RTghsmgWtOANOSxskNN5RJ4rAuFZV0gq73vZuu_Rhs6Iu6Ctp6rxrbDqEghOYMUxrzXxQYg4wJSSM63aO6a0PorCs2XVXHXxeAi53XYue1OHiN-NWheShra37gb5G_V-9Ordqha6KTv7u-ALI2fjE</recordid><startdate>20181226</startdate><enddate>20181226</enddate><creator>Derosa, Joseph</creator><creator>Kleinmans, Roman</creator><creator>Tran, Van T</creator><creator>Karunananda, Malkanthi K</creator><creator>Wisniewski, Steven R</creator><creator>Eastgate, Martin D</creator><creator>Engle, Keary M</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0001-6035-4394</orcidid><orcidid>https://orcid.org/0000-0003-2767-6556</orcidid><orcidid>https://orcid.org/0000-0002-6487-3121</orcidid><orcidid>https://orcid.org/0000-0002-8697-8864</orcidid><orcidid>https://orcid.org/0000-0001-8672-4875</orcidid></search><sort><creationdate>20181226</creationdate><title>Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides</title><author>Derosa, Joseph ; Kleinmans, Roman ; Tran, Van T ; Karunananda, Malkanthi K ; Wisniewski, Steven R ; Eastgate, Martin D ; Engle, Keary M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a357t-1a79902163ff1b8a19c58fffb4df8fa86d5916c62103b303b7d6d3592f0cba393</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkenes - chemical synthesis</topic><topic>amides</topic><topic>Amides - chemical synthesis</topic><topic>Boronic Acids - chemistry</topic><topic>Catalysis</topic><topic>Coordination Complexes - chemistry</topic><topic>cross-coupling reactions</topic><topic>dimethyl fumarate</topic><topic>Dimethyl Fumarate - chemistry</topic><topic>esters</topic><topic>Iodobenzenes - chemistry</topic><topic>Ligands</topic><topic>Models, Chemical</topic><topic>moieties</topic><topic>Nickel - chemistry</topic><topic>olefin</topic><topic>organoiodine compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Derosa, Joseph</creatorcontrib><creatorcontrib>Kleinmans, Roman</creatorcontrib><creatorcontrib>Tran, Van T</creatorcontrib><creatorcontrib>Karunananda, Malkanthi K</creatorcontrib><creatorcontrib>Wisniewski, Steven R</creatorcontrib><creatorcontrib>Eastgate, Martin D</creatorcontrib><creatorcontrib>Engle, Keary M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Derosa, Joseph</au><au>Kleinmans, Roman</au><au>Tran, Van T</au><au>Karunananda, Malkanthi K</au><au>Wisniewski, Steven R</au><au>Eastgate, Martin D</au><au>Engle, Keary M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2018-12-26</date><risdate>2018</risdate><volume>140</volume><issue>51</issue><spage>17878</spage><epage>17883</epage><pages>17878-17883</pages><issn>0002-7863</issn><issn>1520-5126</issn><eissn>1520-5126</eissn><abstract>A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amine are compatible substrates. This method represents the first example of regiocontrolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on the potential substrate binding mode and the role of the EDO ligand in the reductive elimination step.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>30525575</pmid><doi>10.1021/jacs.8b11942</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-6035-4394</orcidid><orcidid>https://orcid.org/0000-0003-2767-6556</orcidid><orcidid>https://orcid.org/0000-0002-6487-3121</orcidid><orcidid>https://orcid.org/0000-0002-8697-8864</orcidid><orcidid>https://orcid.org/0000-0001-8672-4875</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2018-12, Vol.140 (51), p.17878-17883 |
| issn | 0002-7863 1520-5126 1520-5126 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2237503322 |
| source | ACS Publications; MEDLINE |
| subjects | Alkenes - chemical synthesis amides Amides - chemical synthesis Boronic Acids - chemistry Catalysis Coordination Complexes - chemistry cross-coupling reactions dimethyl fumarate Dimethyl Fumarate - chemistry esters Iodobenzenes - chemistry Ligands Models, Chemical moieties Nickel - chemistry olefin organoiodine compounds |
| title | Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-06T07%3A15%3A52IST&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=Nickel-Catalyzed%201,2-Diarylation%20of%20Simple%20Alkenyl%20Amides&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Derosa,%20Joseph&rft.date=2018-12-26&rft.volume=140&rft.issue=51&rft.spage=17878&rft.epage=17883&rft.pages=17878-17883&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/jacs.8b11942&rft_dat=%3Cproquest_cross%3E2237503322%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=2155145893&rft_id=info:pmid/30525575&rfr_iscdi=true |