Photocatalyzed alkylative cyclization of 2-isocyanobiphenyls with unactivated alkyl iodides
We herein report the first photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides. This simple protocol operates under mild reaction conditions and affords 6-alkyl phenanthridines in good yields. To elucidate the reaction mechanism, Stern-Volmer quenching stud...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2022-04, Vol.2 (15), p.3136-3144 |
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| container_issue | 15 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Tripathy, Alisha Rani A, Rizwana Rahmathulla Kumar, Amit Yatham, Veera Reddy |
| description | We herein report the first photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides. This simple protocol operates under mild reaction conditions and affords 6-alkyl phenanthridines in good yields. To elucidate the reaction mechanism, Stern-Volmer quenching studies were carried out and these studies revealed that the photocatalyst is not directly involved in a single electron transfer process with the alkyl iodide.
Photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides was developed. This protocol operates under mild conditions and tolerates a variety of functional groups affording 6-alkyl phenanthridines in good yields. |
| doi_str_mv | 10.1039/d2ob00314g |
| format | Article |
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Photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides was developed. This protocol operates under mild conditions and tolerates a variety of functional groups affording 6-alkyl phenanthridines in good yields.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob00314g</identifier><identifier>PMID: 35343547</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkylation ; Electron transfer ; Electrons ; Iodides ; Reaction mechanisms ; Single electrons</subject><ispartof>Organic & biomolecular chemistry, 2022-04, Vol.2 (15), p.3136-3144</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-c025ce2e84626577123ef719966e512f73bd2aff588c463c8814616deeb0bd913</citedby><cites>FETCH-LOGICAL-c337t-c025ce2e84626577123ef719966e512f73bd2aff588c463c8814616deeb0bd913</cites><orcidid>0000-0002-3967-5342</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35343547$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tripathy, Alisha Rani</creatorcontrib><creatorcontrib>A, Rizwana Rahmathulla</creatorcontrib><creatorcontrib>Kumar, Amit</creatorcontrib><creatorcontrib>Yatham, Veera Reddy</creatorcontrib><title>Photocatalyzed alkylative cyclization of 2-isocyanobiphenyls with unactivated alkyl iodides</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>We herein report the first photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides. This simple protocol operates under mild reaction conditions and affords 6-alkyl phenanthridines in good yields. To elucidate the reaction mechanism, Stern-Volmer quenching studies were carried out and these studies revealed that the photocatalyst is not directly involved in a single electron transfer process with the alkyl iodide.
Photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides was developed. This protocol operates under mild conditions and tolerates a variety of functional groups affording 6-alkyl phenanthridines in good yields.</description><subject>Alkylation</subject><subject>Electron transfer</subject><subject>Electrons</subject><subject>Iodides</subject><subject>Reaction mechanisms</subject><subject>Single electrons</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpd0c9LwzAUB_AgipvTi3el4EWEan41aY86dQrCPOjJQ0mTV5fZNbNple6vt3M_BE95kM97PL4PoWOCLwlmyZWhLsOYEf6-g_qESxniiCW725riHjrwfooxSaTg-6jHIsZZxGUfvT1PXO20qlXRLsAEqvhoC1XbLwh0qwu76GpXBi4PaGi9060qXWbnEyjbwgfftp4ETal016DqTXtgnbEG_CHay1Xh4Wj9DtDr_d3L8CF8Go8eh9dPoWZM1qHGNNJAIeaCikhKQhnkkiSJEBARmkuWGaryPIpjzQXTcUy4IMIAZDgzCWEDdL6aO6_cZwO-TmfWaygKVYJrfEoF50xwSpf07B-duqYqu-2WKhGYM8k7dbFSunLeV5Cn88rOVNWmBKfLyNNbOr75jXzU4dP1yCabgdnSTcYdOFmByuvt79_N2A-BF4Xm</recordid><startdate>20220413</startdate><enddate>20220413</enddate><creator>Tripathy, Alisha Rani</creator><creator>A, Rizwana Rahmathulla</creator><creator>Kumar, Amit</creator><creator>Yatham, Veera Reddy</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3967-5342</orcidid></search><sort><creationdate>20220413</creationdate><title>Photocatalyzed alkylative cyclization of 2-isocyanobiphenyls with unactivated alkyl iodides</title><author>Tripathy, Alisha Rani ; A, Rizwana Rahmathulla ; Kumar, Amit ; Yatham, Veera Reddy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-c025ce2e84626577123ef719966e512f73bd2aff588c463c8814616deeb0bd913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkylation</topic><topic>Electron transfer</topic><topic>Electrons</topic><topic>Iodides</topic><topic>Reaction mechanisms</topic><topic>Single electrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tripathy, Alisha Rani</creatorcontrib><creatorcontrib>A, Rizwana Rahmathulla</creatorcontrib><creatorcontrib>Kumar, Amit</creatorcontrib><creatorcontrib>Yatham, Veera Reddy</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tripathy, Alisha Rani</au><au>A, Rizwana Rahmathulla</au><au>Kumar, Amit</au><au>Yatham, Veera Reddy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalyzed alkylative cyclization of 2-isocyanobiphenyls with unactivated alkyl iodides</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2022-04-13</date><risdate>2022</risdate><volume>2</volume><issue>15</issue><spage>3136</spage><epage>3144</epage><pages>3136-3144</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>We herein report the first photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides. This simple protocol operates under mild reaction conditions and affords 6-alkyl phenanthridines in good yields. To elucidate the reaction mechanism, Stern-Volmer quenching studies were carried out and these studies revealed that the photocatalyst is not directly involved in a single electron transfer process with the alkyl iodide.
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| ispartof | Organic & biomolecular chemistry, 2022-04, Vol.2 (15), p.3136-3144 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Alkylation Electron transfer Electrons Iodides Reaction mechanisms Single electrons |
| title | Photocatalyzed alkylative cyclization of 2-isocyanobiphenyls with unactivated alkyl iodides |
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