Metal-Free Switchable Chemo- and Regioselective Alkylation of Oxindoles Using Secondary Alcohols
In this study, we have disclosed N-alkylation and C-alkylation reactions of 2-oxindoles with secondary alcohols. Interestingly, these chemoselective reactions are tunable by changing the reaction conditions. Utilization of protic solvent and Brønsted acid catalyst afforded C-alkylation, whereas, apr...
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| Veröffentlicht in: | Journal of organic chemistry 2024-08, Vol.89 (16), p.11244-11260 |
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| container_issue | 16 |
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| container_title | Journal of organic chemistry |
| container_volume | 89 |
| creator | Lamba, Manisha Singh, Prasoon Raj Tanmay Goswami, Avijit |
| description | In this study, we have disclosed N-alkylation and C-alkylation reactions of 2-oxindoles with secondary alcohols. Interestingly, these chemoselective reactions are tunable by changing the reaction conditions. Utilization of protic solvent and Brønsted acid catalyst afforded C-alkylation, whereas, aprotic solvent and Lewis acid catalyst afforded N-alkylation of 2-oxindoles in good to excellent yields. Regioselectivity is achieved by protecting the N-center of the oxindole and C5 alkylated product is furnished exclusively. This protocol is notable because it demonstrates functionalization at the C7 position of oxindole without the need for any directing group at the N-center. Further, a new protocol has been reported for C–H oxygenation at the benzylic position of one of the C5 alkylated derivative. |
| doi_str_mv | 10.1021/acs.joc.4c00903 |
| format | Article |
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Interestingly, these chemoselective reactions are tunable by changing the reaction conditions. Utilization of protic solvent and Brønsted acid catalyst afforded C-alkylation, whereas, aprotic solvent and Lewis acid catalyst afforded N-alkylation of 2-oxindoles in good to excellent yields. Regioselectivity is achieved by protecting the N-center of the oxindole and C5 alkylated product is furnished exclusively. This protocol is notable because it demonstrates functionalization at the C7 position of oxindole without the need for any directing group at the N-center. Further, a new protocol has been reported for C–H oxygenation at the benzylic position of one of the C5 alkylated derivative.</description><identifier>ISSN: 0022-3263</identifier><identifier>ISSN: 1520-6904</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.4c00903</identifier><identifier>PMID: 39106447</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>alkylation ; catalysts ; chemoselectivity ; Lewis acids ; organic chemistry ; regioselectivity ; solvents</subject><ispartof>Journal of organic chemistry, 2024-08, Vol.89 (16), p.11244-11260</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a250t-ec932e5e8ba1da86c705f3baca3bdb0a756c3d406816429401c1c4d409f328ed3</cites><orcidid>0000-0003-2798-1956</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/acs.joc.4c00903$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.4c00903$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39106447$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lamba, Manisha</creatorcontrib><creatorcontrib>Singh, Prasoon Raj</creatorcontrib><creatorcontrib>Tanmay</creatorcontrib><creatorcontrib>Goswami, Avijit</creatorcontrib><title>Metal-Free Switchable Chemo- and Regioselective Alkylation of Oxindoles Using Secondary Alcohols</title><title>Journal of organic chemistry</title><addtitle>J. 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Further, a new protocol has been reported for C–H oxygenation at the benzylic position of one of the C5 alkylated derivative.</description><subject>alkylation</subject><subject>catalysts</subject><subject>chemoselectivity</subject><subject>Lewis acids</subject><subject>organic chemistry</subject><subject>regioselectivity</subject><subject>solvents</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkctLw0AQxhdRbH2cvckeBUmdfeVxLMWqUCn4OMfNZtKmbrM1m6r9711p9SbOHAaG33ww30fIGYMBA86utPGDhTMDaQAyEHukzxSHKM5A7pM-AOeR4LHokSPvFxBKKXVIeiJjEEuZ9MnLPXbaRuMWkT5-1J2Z68IiHc1x6SKqm5I-4Kx2Hi2arn5HOrSvG6u72jXUVXT6WTels-jps6-bGX1E45pSt5vAGTd31p-Qg0pbj6e7eUyex9dPo9toMr25Gw0nkeYKughNJjgqTAvNSp3GJgFViUIbLYqyAJ2o2IhSQpyyWPJMAjPMyLDIKsFTLMUxudjqrlr3tkbf5cvaG7RWN-jWPhdMiYRlksX_o5BmaRJaBfRqi5rWed9ila_aehn-yxnk3wnkIYE8JJDvEggX5zvxdbHE8pf_sTwAl1tge7lum2DLn3JfcAqRGg</recordid><startdate>20240816</startdate><enddate>20240816</enddate><creator>Lamba, Manisha</creator><creator>Singh, Prasoon Raj</creator><creator>Tanmay</creator><creator>Goswami, Avijit</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0003-2798-1956</orcidid></search><sort><creationdate>20240816</creationdate><title>Metal-Free Switchable Chemo- and Regioselective Alkylation of Oxindoles Using Secondary Alcohols</title><author>Lamba, Manisha ; Singh, Prasoon Raj ; Tanmay ; Goswami, Avijit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a250t-ec932e5e8ba1da86c705f3baca3bdb0a756c3d406816429401c1c4d409f328ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>alkylation</topic><topic>catalysts</topic><topic>chemoselectivity</topic><topic>Lewis acids</topic><topic>organic chemistry</topic><topic>regioselectivity</topic><topic>solvents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lamba, Manisha</creatorcontrib><creatorcontrib>Singh, Prasoon Raj</creatorcontrib><creatorcontrib>Tanmay</creatorcontrib><creatorcontrib>Goswami, Avijit</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lamba, Manisha</au><au>Singh, Prasoon Raj</au><au>Tanmay</au><au>Goswami, Avijit</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-Free Switchable Chemo- and Regioselective Alkylation of Oxindoles Using Secondary Alcohols</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2024-08-16</date><risdate>2024</risdate><volume>89</volume><issue>16</issue><spage>11244</spage><epage>11260</epage><pages>11244-11260</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>In this study, we have disclosed N-alkylation and C-alkylation reactions of 2-oxindoles with secondary alcohols. Interestingly, these chemoselective reactions are tunable by changing the reaction conditions. Utilization of protic solvent and Brønsted acid catalyst afforded C-alkylation, whereas, aprotic solvent and Lewis acid catalyst afforded N-alkylation of 2-oxindoles in good to excellent yields. Regioselectivity is achieved by protecting the N-center of the oxindole and C5 alkylated product is furnished exclusively. This protocol is notable because it demonstrates functionalization at the C7 position of oxindole without the need for any directing group at the N-center. 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| subjects | alkylation catalysts chemoselectivity Lewis acids organic chemistry regioselectivity solvents |
| title | Metal-Free Switchable Chemo- and Regioselective Alkylation of Oxindoles Using Secondary Alcohols |
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