Synthesis of 2,3‐Disubstituted Indoles by Nickel(0)‐Catalyzed Migratory Cycloisomerization of o‐Alkynylanilides
We herein report a nickel‐catalyzed migratory cycloisomerization of o‐alkynylanilides, giving 2,3‐disubstituted indoles in good yields. The cyclization proceeded via acyl transfer on the nitrogen atom of the substrate to C3‐position in the product, and an N‐heterocyclic carbene (NHC) ligand such as...
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| Veröffentlicht in: | Asian journal of organic chemistry 2023-07, Vol.12 (7), p.n/a |
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| container_title | Asian journal of organic chemistry |
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| creator | Koshiba, Mikiko Furuki, Yuto Morisaki, Kazuhiro Doi, Ryohei Sato, Yoshihiro |
| description | We herein report a nickel‐catalyzed migratory cycloisomerization of o‐alkynylanilides, giving 2,3‐disubstituted indoles in good yields. The cyclization proceeded via acyl transfer on the nitrogen atom of the substrate to C3‐position in the product, and an N‐heterocyclic carbene (NHC) ligand such as ICy or SICy was found to be suitable in this reaction. It was thought that the reaction proceeds via an aza‐nickelcyclepentene intermediate formed from alkyne and the C=O bond of the amide moiety in o‐alkynylanilides.
A nickel‐catalyzed migratory cycloisomerization of o‐alkynylanilides was investigated, and it was found to give 2,3‐disubstituted indoles. The cyclization was thought to proceed via an aza‐nickelcyclepentene intermediate formed from alkyne and the C=O bond amide moiety in the substrate, accompanied by acyl transfer on the nitrogen atom to the C3 position in the product. |
| doi_str_mv | 10.1002/ajoc.202300272 |
| format | Article |
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A nickel‐catalyzed migratory cycloisomerization of o‐alkynylanilides was investigated, and it was found to give 2,3‐disubstituted indoles. The cyclization was thought to proceed via an aza‐nickelcyclepentene intermediate formed from alkyne and the C=O bond amide moiety in the substrate, accompanied by acyl transfer on the nitrogen atom to the C3 position in the product.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202300272</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Cycloisomerization ; Indole ; Indoles ; Isomerization ; Migration ; NHC ; Nickel ; Organic chemistry ; Substrates</subject><ispartof>Asian journal of organic chemistry, 2023-07, Vol.12 (7), p.n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2722-da234c3f35a241ff28163870e3ffe496f219af01728e90cdc1ea68f9c8d612963</cites><orcidid>0000-0002-5692-4726 ; 0000-0001-8285-0209 ; 0000-0003-2540-5525</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%2Fajoc.202300272$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202300272$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Koshiba, Mikiko</creatorcontrib><creatorcontrib>Furuki, Yuto</creatorcontrib><creatorcontrib>Morisaki, Kazuhiro</creatorcontrib><creatorcontrib>Doi, Ryohei</creatorcontrib><creatorcontrib>Sato, Yoshihiro</creatorcontrib><title>Synthesis of 2,3‐Disubstituted Indoles by Nickel(0)‐Catalyzed Migratory Cycloisomerization of o‐Alkynylanilides</title><title>Asian journal of organic chemistry</title><description>We herein report a nickel‐catalyzed migratory cycloisomerization of o‐alkynylanilides, giving 2,3‐disubstituted indoles in good yields. The cyclization proceeded via acyl transfer on the nitrogen atom of the substrate to C3‐position in the product, and an N‐heterocyclic carbene (NHC) ligand such as ICy or SICy was found to be suitable in this reaction. It was thought that the reaction proceeds via an aza‐nickelcyclepentene intermediate formed from alkyne and the C=O bond of the amide moiety in o‐alkynylanilides.
A nickel‐catalyzed migratory cycloisomerization of o‐alkynylanilides was investigated, and it was found to give 2,3‐disubstituted indoles. The cyclization was thought to proceed via an aza‐nickelcyclepentene intermediate formed from alkyne and the C=O bond amide moiety in the substrate, accompanied by acyl transfer on the nitrogen atom to the C3 position in the product.</description><subject>Alkynes</subject><subject>Cycloisomerization</subject><subject>Indole</subject><subject>Indoles</subject><subject>Isomerization</subject><subject>Migration</subject><subject>NHC</subject><subject>Nickel</subject><subject>Organic chemistry</subject><subject>Substrates</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOwzAQRSMEEhV0yzoSG5BI8SNN7GUVXkWFLoB15Do2uHXjYjtC7opP4Bv5ElwVlSWzmRnp3BndmyQnEAwgAOiSzQ0fIIBwXEq0l_QQpDgbEjjc382gPEz6zs1BrLKkENFe0j2F1r8Jp1xqZIou8Pfn15Vy3cx55TsvmnTcNkYLl85C-qj4QugzcB6hinmmwzoCD-rVMm9sSKvAtVHOLIVVa-aVaTdHTaRHehHaoFmrtGqEO04OJNNO9H_7UfJyc_1c3WWT6e24Gk0yHk2grGEI5xxLPGQoh1IiAgtMSiCwlCKnhYzGmASwRERQwBsOBSuIpJw0RXRX4KPkdHt3Zc17J5yv56azbXxZI5JDRCiCOFKDLcWtcc4KWa-sWjIbagjqTbr1Jt16l24U0K3gQ2kR_qHr0f20-tP-AC-Xgco</recordid><startdate>202307</startdate><enddate>202307</enddate><creator>Koshiba, Mikiko</creator><creator>Furuki, Yuto</creator><creator>Morisaki, Kazuhiro</creator><creator>Doi, Ryohei</creator><creator>Sato, Yoshihiro</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-5692-4726</orcidid><orcidid>https://orcid.org/0000-0001-8285-0209</orcidid><orcidid>https://orcid.org/0000-0003-2540-5525</orcidid></search><sort><creationdate>202307</creationdate><title>Synthesis of 2,3‐Disubstituted Indoles by Nickel(0)‐Catalyzed Migratory Cycloisomerization of o‐Alkynylanilides</title><author>Koshiba, Mikiko ; Furuki, Yuto ; Morisaki, Kazuhiro ; Doi, Ryohei ; Sato, Yoshihiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2722-da234c3f35a241ff28163870e3ffe496f219af01728e90cdc1ea68f9c8d612963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkynes</topic><topic>Cycloisomerization</topic><topic>Indole</topic><topic>Indoles</topic><topic>Isomerization</topic><topic>Migration</topic><topic>NHC</topic><topic>Nickel</topic><topic>Organic chemistry</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Koshiba, Mikiko</creatorcontrib><creatorcontrib>Furuki, Yuto</creatorcontrib><creatorcontrib>Morisaki, Kazuhiro</creatorcontrib><creatorcontrib>Doi, Ryohei</creatorcontrib><creatorcontrib>Sato, Yoshihiro</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Koshiba, Mikiko</au><au>Furuki, Yuto</au><au>Morisaki, Kazuhiro</au><au>Doi, Ryohei</au><au>Sato, Yoshihiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2,3‐Disubstituted Indoles by Nickel(0)‐Catalyzed Migratory Cycloisomerization of o‐Alkynylanilides</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2023-07</date><risdate>2023</risdate><volume>12</volume><issue>7</issue><epage>n/a</epage><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>We herein report a nickel‐catalyzed migratory cycloisomerization of o‐alkynylanilides, giving 2,3‐disubstituted indoles in good yields. The cyclization proceeded via acyl transfer on the nitrogen atom of the substrate to C3‐position in the product, and an N‐heterocyclic carbene (NHC) ligand such as ICy or SICy was found to be suitable in this reaction. It was thought that the reaction proceeds via an aza‐nickelcyclepentene intermediate formed from alkyne and the C=O bond of the amide moiety in o‐alkynylanilides.
A nickel‐catalyzed migratory cycloisomerization of o‐alkynylanilides was investigated, and it was found to give 2,3‐disubstituted indoles. The cyclization was thought to proceed via an aza‐nickelcyclepentene intermediate formed from alkyne and the C=O bond amide moiety in the substrate, accompanied by acyl transfer on the nitrogen atom to the C3 position in the product.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202300272</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-5692-4726</orcidid><orcidid>https://orcid.org/0000-0001-8285-0209</orcidid><orcidid>https://orcid.org/0000-0003-2540-5525</orcidid></addata></record> |
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| subjects | Alkynes Cycloisomerization Indole Indoles Isomerization Migration NHC Nickel Organic chemistry Substrates |
| title | Synthesis of 2,3‐Disubstituted Indoles by Nickel(0)‐Catalyzed Migratory Cycloisomerization of o‐Alkynylanilides |
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