Photochemically-Mediated, Nickel-Catalyzed Synthesis of N‑(Hetero)aryl Sulfamate Esters
A general method is described for the coupling of (hetero)aryl bromides with O-alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range o...
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| Veröffentlicht in: | Organic letters 2019-09, Vol.21 (17), p.7049-7054 |
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| container_title | Organic letters |
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| creator | Blackburn, J. Miles Gant Kanegusuku, Anastasia L Scott, Georgia E Roizen, Jennifer L |
| description | A general method is described for the coupling of (hetero)aryl bromides with O-alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range of simple and complex O-alkyl sulfamate ester substrates under mild conditions. Furthermore, it is possible to avoid undesirable N-alkylation, which was found to plague palladium-based protocols for N-arylation of O-alkyl sulfamate esters. These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C–N coupling processes. |
| doi_str_mv | 10.1021/acs.orglett.9b02621 |
| format | Article |
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These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C–N coupling processes.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.9b02621</identifier><identifier>PMID: 31436104</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Esters - chemical synthesis ; Esters - chemistry ; Molecular Structure ; Nickel - chemistry ; Photochemical Processes ; Sulfonic Acids - chemical synthesis ; Sulfonic Acids - chemistry</subject><ispartof>Organic letters, 2019-09, Vol.21 (17), p.7049-7054</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-1bffebdc9c3dd8f81032cf4a03332126a37e5acef1dbd62621858ae38d80666e3</citedby><cites>FETCH-LOGICAL-a445t-1bffebdc9c3dd8f81032cf4a03332126a37e5acef1dbd62621858ae38d80666e3</cites><orcidid>0000-0001-9961-6398 ; 0000-0002-6053-5512</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.orglett.9b02621$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.9b02621$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31436104$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Blackburn, J. 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These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C–N coupling processes.</description><subject>Catalysis</subject><subject>Esters - chemical synthesis</subject><subject>Esters - chemistry</subject><subject>Molecular Structure</subject><subject>Nickel - chemistry</subject><subject>Photochemical Processes</subject><subject>Sulfonic Acids - chemical synthesis</subject><subject>Sulfonic Acids - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UctOIzEQtNAi3l-AhOYI0k7wY8aZXJBWEbsg8ZKAAyfLY7fJgGectT1I4bS_wC_yJThKiOCyp261q6rLXQjtEzwgmJJjqcLA-UcLMQ5GNaackjW0RUrK8iEu6Y9Vz_Em2g7hCWOSJqMNtMlIwTjBxRZ6uJm46NQE2kZJa2f5JehGRtA_s6tGPYPNxzJKO3sFnd3OujiB0ITMmezq_d_b4RlE8O5I-pnNbntrZJuo2WlI07CL1o20AfaWdQfd_z69G5_lF9d_zse_LnJZFGXMSW0M1FqNFNO6MhXBjCpTSMwYo4RyyYZQSgWG6Frz-SerspLAKl1hzjmwHXSy0J32dQtaQRe9tGLqmzb5Ek424vtL10zEo3sRQ1qQZCEJHC4FvPvbQ4iibYICa2UHrg-CMsZHVZlumaBsAVXeheDBrNYQLOahiBSKWIYilqEk1sFXhyvOZwoJcLwAzNlPrvddOth_JT8AESaenA</recordid><startdate>20190906</startdate><enddate>20190906</enddate><creator>Blackburn, J. 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Miles</creatorcontrib><creatorcontrib>Gant Kanegusuku, Anastasia L</creatorcontrib><creatorcontrib>Scott, Georgia E</creatorcontrib><creatorcontrib>Roizen, Jennifer L</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Blackburn, J. 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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2019-09, Vol.21 (17), p.7049-7054 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Catalysis Esters - chemical synthesis Esters - chemistry Molecular Structure Nickel - chemistry Photochemical Processes Sulfonic Acids - chemical synthesis Sulfonic Acids - chemistry |
| title | Photochemically-Mediated, Nickel-Catalyzed Synthesis of N‑(Hetero)aryl Sulfamate Esters |
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