Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins
Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. However, these reactions often require transition-metal catalysis, and are mainly limited to 1,2-carboamination. Herein, we report a novel radical r...
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| Veröffentlicht in: | Chemical science (Cambridge) 2023-03, Vol.14 (9), p.2447-2454 |
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| creator | Tan, Guangying Paulus, Fritz Petti, Alessia Wiethoff, Maxim-Aleksa Lauer, Anna Daniliuc, Constantin Glorius, Frank |
| description | Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. However, these reactions often require transition-metal catalysis, and are mainly limited to 1,2-carboamination. Herein, we report a novel radical relay 1,4-carboimination across two distinct olefins with alkyl carboxylic acid-derived bifunctional oxime esters
via
energy transfer catalysis. The reaction is highly chemo- and regioselective, and multiple C-C and C-N bonds were formed in a single orchestrated operation. This mild and metal-free method features a remarkably broad substrate scope with excellent tolerance of sensitive functional groups, therefore providing easy access to structurally diverse 1,4-carboiminated products. Moreover, the obtained imines could be easily converted into valuable biologically relevant free γ-amino acids.
Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. |
| doi_str_mv | 10.1039/d2sc06497a |
| format | Article |
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via
energy transfer catalysis. The reaction is highly chemo- and regioselective, and multiple C-C and C-N bonds were formed in a single orchestrated operation. This mild and metal-free method features a remarkably broad substrate scope with excellent tolerance of sensitive functional groups, therefore providing easy access to structurally diverse 1,4-carboiminated products. Moreover, the obtained imines could be easily converted into valuable biologically relevant free γ-amino acids.
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via
energy transfer catalysis. The reaction is highly chemo- and regioselective, and multiple C-C and C-N bonds were formed in a single orchestrated operation. This mild and metal-free method features a remarkably broad substrate scope with excellent tolerance of sensitive functional groups, therefore providing easy access to structurally diverse 1,4-carboiminated products. Moreover, the obtained imines could be easily converted into valuable biologically relevant free γ-amino acids.
Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks.</description><subject>Alkenes</subject><subject>Amines</subject><subject>Amino acids</subject><subject>Carboxylic acids</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Energy transfer</subject><subject>Esters</subject><subject>Functional groups</subject><subject>Imines</subject><subject>Relay</subject><subject>Substrates</subject><subject>Transition metals</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkUFLJDEQhYMoKurFu0vDXhbZdtNJupNchGF0XUHxsIrHkEkqa6QnGZPMivvr7XF0XK1LFbyPR1U9hPYbfNRgKn9Ykg3umOR6DW0TzJq6a6lcX80Eb6G9nO_xUJQ2LeGbaIt2glPB2Da6vYSi-9olgGp2F0vMELIv_h_YKmnrje6rBL1-qprvrDY6TaKf-qCLj6HSJsWcq_IYK-tz8cGUKvbgfMi7aMPpPsPea99BNz9Pr8e_6ours_Px6KI2jIhSd3KiBbdSdqKVLXTaSm2dE46QQerEhAAnQrbUYk6YZdYQ11KOnSBAKMN0Bx0vfWfzyRSsgVCS7tUs-alOTypqrz4qwd-pP_GvkpJz1vLB4NurQYoPc8hFTX020Pc6QJxnRbigXOK2awb06yf0Ps5TGM5bUJjjhvCF4eGSenlOArdapsFqEZk6Ib_HL5GNBvjL_-uv0LeABuBgCaRsVup75vQZGKubqg</recordid><startdate>20230301</startdate><enddate>20230301</enddate><creator>Tan, Guangying</creator><creator>Paulus, Fritz</creator><creator>Petti, Alessia</creator><creator>Wiethoff, Maxim-Aleksa</creator><creator>Lauer, Anna</creator><creator>Daniliuc, Constantin</creator><creator>Glorius, Frank</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-0648-956X</orcidid></search><sort><creationdate>20230301</creationdate><title>Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins</title><author>Tan, Guangying ; Paulus, Fritz ; Petti, Alessia ; Wiethoff, Maxim-Aleksa ; Lauer, Anna ; Daniliuc, Constantin ; Glorius, Frank</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-69ba87d9968595e6ad9adff8f2269b68b2e728953d0724d4dc2f5370f82e23403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkenes</topic><topic>Amines</topic><topic>Amino acids</topic><topic>Carboxylic acids</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Energy transfer</topic><topic>Esters</topic><topic>Functional groups</topic><topic>Imines</topic><topic>Relay</topic><topic>Substrates</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tan, Guangying</creatorcontrib><creatorcontrib>Paulus, Fritz</creatorcontrib><creatorcontrib>Petti, Alessia</creatorcontrib><creatorcontrib>Wiethoff, Maxim-Aleksa</creatorcontrib><creatorcontrib>Lauer, Anna</creatorcontrib><creatorcontrib>Daniliuc, Constantin</creatorcontrib><creatorcontrib>Glorius, Frank</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tan, Guangying</au><au>Paulus, Fritz</au><au>Petti, Alessia</au><au>Wiethoff, Maxim-Aleksa</au><au>Lauer, Anna</au><au>Daniliuc, Constantin</au><au>Glorius, Frank</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2023-03-01</date><risdate>2023</risdate><volume>14</volume><issue>9</issue><spage>2447</spage><epage>2454</epage><pages>2447-2454</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. However, these reactions often require transition-metal catalysis, and are mainly limited to 1,2-carboamination. Herein, we report a novel radical relay 1,4-carboimination across two distinct olefins with alkyl carboxylic acid-derived bifunctional oxime esters
via
energy transfer catalysis. The reaction is highly chemo- and regioselective, and multiple C-C and C-N bonds were formed in a single orchestrated operation. This mild and metal-free method features a remarkably broad substrate scope with excellent tolerance of sensitive functional groups, therefore providing easy access to structurally diverse 1,4-carboiminated products. Moreover, the obtained imines could be easily converted into valuable biologically relevant free γ-amino acids.
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| ispartof | Chemical science (Cambridge), 2023-03, Vol.14 (9), p.2447-2454 |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Alkenes Amines Amino acids Carboxylic acids Catalysis Chemistry Energy transfer Esters Functional groups Imines Relay Substrates Transition metals |
| title | Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins |
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