Synthesis of 3,3-disubstituted allyl isoindolinones via Pd-catalyzed decarboxylative allylic alkylation
[Display omitted] •A mild and high-yielding decarboxylative coupling reaction of isoindolinones was developed.•The reaction is tolerant of a range of functional groups, including those bearing relatively acidic protons.•The coupling reaction is leveraged to access the bioactive indolizidine framewor...
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| Veröffentlicht in: | Tetrahedron letters 2024-09, Vol.148, p.155242, Article 155242 |
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| creator | Alvarado, Mario Loo, Marisa Adler, Hanna Arnall, Caroline Amsden, Katharine Martinez, Gisela Navarro, Raul |
| description | [Display omitted]
•A mild and high-yielding decarboxylative coupling reaction of isoindolinones was developed.•The reaction is tolerant of a range of functional groups, including those bearing relatively acidic protons.•The coupling reaction is leveraged to access the bioactive indolizidine framework.
Herein, we report a mild palladium-catalyzed decarboxylative allylic alkylation of allyl ester-substituted isoindolinone substrates to afford a variety of 3,3-disubstituted isoindolinone derivatives. The decarboxylative coupling reaction tolerates a range of functional groups, including ketones and alkenyl halides, and does not require protection of the isoindolinone nitrogen. Additionally, the reaction was found to proceed in near-quantitative yield for most substrates evaluated. Based on the isolation of competing cyclopropane and protonation products, a reaction mechanism is proposed. |
| doi_str_mv | 10.1016/j.tetlet.2024.155242 |
| format | Article |
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•A mild and high-yielding decarboxylative coupling reaction of isoindolinones was developed.•The reaction is tolerant of a range of functional groups, including those bearing relatively acidic protons.•The coupling reaction is leveraged to access the bioactive indolizidine framework.
Herein, we report a mild palladium-catalyzed decarboxylative allylic alkylation of allyl ester-substituted isoindolinone substrates to afford a variety of 3,3-disubstituted isoindolinone derivatives. The decarboxylative coupling reaction tolerates a range of functional groups, including ketones and alkenyl halides, and does not require protection of the isoindolinone nitrogen. Additionally, the reaction was found to proceed in near-quantitative yield for most substrates evaluated. Based on the isolation of competing cyclopropane and protonation products, a reaction mechanism is proposed.</description><identifier>ISSN: 0040-4039</identifier><identifier>DOI: 10.1016/j.tetlet.2024.155242</identifier><identifier>PMID: 39183729</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Allylation ; Decarboxylative ; Isoindolinones ; Palladium-catalyzed</subject><ispartof>Tetrahedron letters, 2024-09, Vol.148, p.155242, Article 155242</ispartof><rights>2024 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c241t-1ff9358767feb09893fa4821e5b175d2d7b09a19118e7a015aae5eaf21564dad3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2024.155242$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39183729$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Alvarado, Mario</creatorcontrib><creatorcontrib>Loo, Marisa</creatorcontrib><creatorcontrib>Adler, Hanna</creatorcontrib><creatorcontrib>Arnall, Caroline</creatorcontrib><creatorcontrib>Amsden, Katharine</creatorcontrib><creatorcontrib>Martinez, Gisela</creatorcontrib><creatorcontrib>Navarro, Raul</creatorcontrib><title>Synthesis of 3,3-disubstituted allyl isoindolinones via Pd-catalyzed decarboxylative allylic alkylation</title><title>Tetrahedron letters</title><addtitle>Tetrahedron Lett</addtitle><description>[Display omitted]
•A mild and high-yielding decarboxylative coupling reaction of isoindolinones was developed.•The reaction is tolerant of a range of functional groups, including those bearing relatively acidic protons.•The coupling reaction is leveraged to access the bioactive indolizidine framework.
Herein, we report a mild palladium-catalyzed decarboxylative allylic alkylation of allyl ester-substituted isoindolinone substrates to afford a variety of 3,3-disubstituted isoindolinone derivatives. The decarboxylative coupling reaction tolerates a range of functional groups, including ketones and alkenyl halides, and does not require protection of the isoindolinone nitrogen. Additionally, the reaction was found to proceed in near-quantitative yield for most substrates evaluated. Based on the isolation of competing cyclopropane and protonation products, a reaction mechanism is proposed.</description><subject>Allylation</subject><subject>Decarboxylative</subject><subject>Isoindolinones</subject><subject>Palladium-catalyzed</subject><issn>0040-4039</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kE1P3DAQhn1o1d0u_IMK5cihWTz-yMcFqVq1gIQEUuFsOfak9eKNIXZWDb--WbL02LmMNHreGc1DyBega6BQXGzXCZPHtGaUiTVIyQT7QJaUCpoLyusF-Rzjlk5VVPQTWfAaKl6yekl-_Ry79Buji1loM_6V59bFoYnJpSGhzbT3o89cDK6zwbsudBizvdPZvc2NTtqPrxNl0ei-CX9Gr5Pb45xyZupPb6PQnZCPrfYRT499RR5_fH_YXOe3d1c3m2-3uWECUg5tW3NZlUXZYkPrquatFhUDlA2U0jJbTlMNNUCFpaYgtUaJumUgC2G15StyPu997sPLgDGpnYsGvdcdhiEqTusSJBSlmFAxo6YPMfbYqufe7XQ_KqDqoFVt1axVHbSqWesUOzteGJod2n-hd6cTcDkDOP25d9iraBx2Bq3r0SRlg_v_hb9tQI7M</recordid><startdate>20240919</startdate><enddate>20240919</enddate><creator>Alvarado, Mario</creator><creator>Loo, Marisa</creator><creator>Adler, Hanna</creator><creator>Arnall, Caroline</creator><creator>Amsden, Katharine</creator><creator>Martinez, Gisela</creator><creator>Navarro, Raul</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20240919</creationdate><title>Synthesis of 3,3-disubstituted allyl isoindolinones via Pd-catalyzed decarboxylative allylic alkylation</title><author>Alvarado, Mario ; Loo, Marisa ; Adler, Hanna ; Arnall, Caroline ; Amsden, Katharine ; Martinez, Gisela ; Navarro, Raul</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c241t-1ff9358767feb09893fa4821e5b175d2d7b09a19118e7a015aae5eaf21564dad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Allylation</topic><topic>Decarboxylative</topic><topic>Isoindolinones</topic><topic>Palladium-catalyzed</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alvarado, Mario</creatorcontrib><creatorcontrib>Loo, Marisa</creatorcontrib><creatorcontrib>Adler, Hanna</creatorcontrib><creatorcontrib>Arnall, Caroline</creatorcontrib><creatorcontrib>Amsden, Katharine</creatorcontrib><creatorcontrib>Martinez, Gisela</creatorcontrib><creatorcontrib>Navarro, Raul</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alvarado, Mario</au><au>Loo, Marisa</au><au>Adler, Hanna</au><au>Arnall, Caroline</au><au>Amsden, Katharine</au><au>Martinez, Gisela</au><au>Navarro, Raul</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 3,3-disubstituted allyl isoindolinones via Pd-catalyzed decarboxylative allylic alkylation</atitle><jtitle>Tetrahedron letters</jtitle><addtitle>Tetrahedron Lett</addtitle><date>2024-09-19</date><risdate>2024</risdate><volume>148</volume><spage>155242</spage><pages>155242-</pages><artnum>155242</artnum><issn>0040-4039</issn><abstract>[Display omitted]
•A mild and high-yielding decarboxylative coupling reaction of isoindolinones was developed.•The reaction is tolerant of a range of functional groups, including those bearing relatively acidic protons.•The coupling reaction is leveraged to access the bioactive indolizidine framework.
Herein, we report a mild palladium-catalyzed decarboxylative allylic alkylation of allyl ester-substituted isoindolinone substrates to afford a variety of 3,3-disubstituted isoindolinone derivatives. The decarboxylative coupling reaction tolerates a range of functional groups, including ketones and alkenyl halides, and does not require protection of the isoindolinone nitrogen. Additionally, the reaction was found to proceed in near-quantitative yield for most substrates evaluated. Based on the isolation of competing cyclopropane and protonation products, a reaction mechanism is proposed.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>39183729</pmid><doi>10.1016/j.tetlet.2024.155242</doi></addata></record> |
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| subjects | Allylation Decarboxylative Isoindolinones Palladium-catalyzed |
| title | Synthesis of 3,3-disubstituted allyl isoindolinones via Pd-catalyzed decarboxylative allylic alkylation |
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