Photoinduced Nickel‐Catalyzed Carbon–Heteroatom Coupling
Herein, we report visible light‐promoted single nickel catalysis for diverse carbon–heteroatom couplings under mild conditions. This mild, general, and robust method to couple diverse nitrogen, oxygen, and sulfur nucleophiles with aryl(heteroaryl)/alkenyl iodides/bromides exhibits a wide functional...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2023-01, Vol.29 (1), p.e202202385-n/a |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | n/a |
|---|---|
| container_issue | 1 |
| container_start_page | e202202385 |
| container_title | Chemistry : a European journal |
| container_volume | 29 |
| creator | Luo, Hang Wang, Guohua Feng, Yunhui Zheng, Wanyao Kong, Lingya Ma, Yunpeng Matsunaga, Shigeki Lin, Luqing |
| description | Herein, we report visible light‐promoted single nickel catalysis for diverse carbon–heteroatom couplings under mild conditions. This mild, general, and robust method to couple diverse nitrogen, oxygen, and sulfur nucleophiles with aryl(heteroaryl)/alkenyl iodides/bromides exhibits a wide functional group tolerance and is applicable to late‐stage modification of pharmaceuticals and natural products. On the base of preliminary mechanistic studies, a NiI/NiIII cycle via the generation of active NiI complexes that appear from homolysis of NiII−I rather than NiII−aryl bond was tentatively proposed.
Exogenous photocatalyst‐free, single nickel‐catalyzed carbon–heteroatom coupling under visible‐light irradiation is reported. Over 15 classes of nucleophile can efficiently couple with aryl/alkene halides to afford valuable heteroatomic arenes/alkenes. The unprecedentedly broad substrate scope and late‐stage modification of valuable molecules fully demonstrate the benefits of the method. |
| doi_str_mv | 10.1002/chem.202202385 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2723485763</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2723485763</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3035-8dacf2df63d194367c95b2e4af9fe7147304246f2d27c220416c0e681ee37b473</originalsourceid><addsrcrecordid>eNqFkE1Lw0AQhhdRbK1ePYrgxUvqfm8XvEioVqgfBz2HzWZiU5NszQdST_0Jgv-wv8QtrRW8CAMDM8-8zPsidExwn2BML-wEij7F1BcbiB3UJYKSgCkpdlEXa64CKZjuoIO6nmKMtWRsH3WYpIRLIbvo8nHiGpeVSWshOb3P7Cvky8VnaBqTzz_8KDRV7Mrl4msEDVTONK44DV07y7Py5RDtpSav4WjTe-j5evgUjoLxw81teDUOLMNMBIPE2JQmqWQJ0ZxJZbWIKXCT6hQU4YphTrn0CFXWO-FEWgxyQACYiv26h87XurPKvbVQN1GR1Rby3JTg2jqiijI-EMqb66GzP-jUtVXpv_OUYooLoYmn-mvKVq6uK0ijWZUVpppHBEerXKNVrtE2V39wspFt4wKSLf4TpAf0GnjPcpj_IxeFo-Hdr_g3uWmEiA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2773745591</pqid></control><display><type>article</type><title>Photoinduced Nickel‐Catalyzed Carbon–Heteroatom Coupling</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Luo, Hang ; Wang, Guohua ; Feng, Yunhui ; Zheng, Wanyao ; Kong, Lingya ; Ma, Yunpeng ; Matsunaga, Shigeki ; Lin, Luqing</creator><creatorcontrib>Luo, Hang ; Wang, Guohua ; Feng, Yunhui ; Zheng, Wanyao ; Kong, Lingya ; Ma, Yunpeng ; Matsunaga, Shigeki ; Lin, Luqing</creatorcontrib><description>Herein, we report visible light‐promoted single nickel catalysis for diverse carbon–heteroatom couplings under mild conditions. This mild, general, and robust method to couple diverse nitrogen, oxygen, and sulfur nucleophiles with aryl(heteroaryl)/alkenyl iodides/bromides exhibits a wide functional group tolerance and is applicable to late‐stage modification of pharmaceuticals and natural products. On the base of preliminary mechanistic studies, a NiI/NiIII cycle via the generation of active NiI complexes that appear from homolysis of NiII−I rather than NiII−aryl bond was tentatively proposed.
Exogenous photocatalyst‐free, single nickel‐catalyzed carbon–heteroatom coupling under visible‐light irradiation is reported. Over 15 classes of nucleophile can efficiently couple with aryl/alkene halides to afford valuable heteroatomic arenes/alkenes. The unprecedentedly broad substrate scope and late‐stage modification of valuable molecules fully demonstrate the benefits of the method.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202202385</identifier><identifier>PMID: 36214656</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aromatic compounds ; Biological Products ; Bromides ; Carbon ; Carbon - chemistry ; carbon–heteroatom bonds ; Catalysis ; Chemistry ; Couplings ; cross-coupling ; Functional groups ; Iodides ; Natural products ; Nickel ; Nickel - chemistry ; nickel catalysis ; Nucleophiles ; Oxygen - chemistry ; reductive elimination ; Sulfur ; visible-light</subject><ispartof>Chemistry : a European journal, 2023-01, Vol.29 (1), p.e202202385-n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><rights>2022 Wiley-VCH GmbH.</rights><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3035-8dacf2df63d194367c95b2e4af9fe7147304246f2d27c220416c0e681ee37b473</citedby><cites>FETCH-LOGICAL-c3035-8dacf2df63d194367c95b2e4af9fe7147304246f2d27c220416c0e681ee37b473</cites><orcidid>0000-0002-4738-0886</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.202202385$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202202385$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36214656$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Luo, Hang</creatorcontrib><creatorcontrib>Wang, Guohua</creatorcontrib><creatorcontrib>Feng, Yunhui</creatorcontrib><creatorcontrib>Zheng, Wanyao</creatorcontrib><creatorcontrib>Kong, Lingya</creatorcontrib><creatorcontrib>Ma, Yunpeng</creatorcontrib><creatorcontrib>Matsunaga, Shigeki</creatorcontrib><creatorcontrib>Lin, Luqing</creatorcontrib><title>Photoinduced Nickel‐Catalyzed Carbon–Heteroatom Coupling</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Herein, we report visible light‐promoted single nickel catalysis for diverse carbon–heteroatom couplings under mild conditions. This mild, general, and robust method to couple diverse nitrogen, oxygen, and sulfur nucleophiles with aryl(heteroaryl)/alkenyl iodides/bromides exhibits a wide functional group tolerance and is applicable to late‐stage modification of pharmaceuticals and natural products. On the base of preliminary mechanistic studies, a NiI/NiIII cycle via the generation of active NiI complexes that appear from homolysis of NiII−I rather than NiII−aryl bond was tentatively proposed.
Exogenous photocatalyst‐free, single nickel‐catalyzed carbon–heteroatom coupling under visible‐light irradiation is reported. Over 15 classes of nucleophile can efficiently couple with aryl/alkene halides to afford valuable heteroatomic arenes/alkenes. The unprecedentedly broad substrate scope and late‐stage modification of valuable molecules fully demonstrate the benefits of the method.</description><subject>Aromatic compounds</subject><subject>Biological Products</subject><subject>Bromides</subject><subject>Carbon</subject><subject>Carbon - chemistry</subject><subject>carbon–heteroatom bonds</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Couplings</subject><subject>cross-coupling</subject><subject>Functional groups</subject><subject>Iodides</subject><subject>Natural products</subject><subject>Nickel</subject><subject>Nickel - chemistry</subject><subject>nickel catalysis</subject><subject>Nucleophiles</subject><subject>Oxygen - chemistry</subject><subject>reductive elimination</subject><subject>Sulfur</subject><subject>visible-light</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1Lw0AQhhdRbK1ePYrgxUvqfm8XvEioVqgfBz2HzWZiU5NszQdST_0Jgv-wv8QtrRW8CAMDM8-8zPsidExwn2BML-wEij7F1BcbiB3UJYKSgCkpdlEXa64CKZjuoIO6nmKMtWRsH3WYpIRLIbvo8nHiGpeVSWshOb3P7Cvky8VnaBqTzz_8KDRV7Mrl4msEDVTONK44DV07y7Py5RDtpSav4WjTe-j5evgUjoLxw81teDUOLMNMBIPE2JQmqWQJ0ZxJZbWIKXCT6hQU4YphTrn0CFXWO-FEWgxyQACYiv26h87XurPKvbVQN1GR1Rby3JTg2jqiijI-EMqb66GzP-jUtVXpv_OUYooLoYmn-mvKVq6uK0ijWZUVpppHBEerXKNVrtE2V39wspFt4wKSLf4TpAf0GnjPcpj_IxeFo-Hdr_g3uWmEiA</recordid><startdate>20230102</startdate><enddate>20230102</enddate><creator>Luo, Hang</creator><creator>Wang, Guohua</creator><creator>Feng, Yunhui</creator><creator>Zheng, Wanyao</creator><creator>Kong, Lingya</creator><creator>Ma, Yunpeng</creator><creator>Matsunaga, Shigeki</creator><creator>Lin, Luqing</creator><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-4738-0886</orcidid></search><sort><creationdate>20230102</creationdate><title>Photoinduced Nickel‐Catalyzed Carbon–Heteroatom Coupling</title><author>Luo, Hang ; Wang, Guohua ; Feng, Yunhui ; Zheng, Wanyao ; Kong, Lingya ; Ma, Yunpeng ; Matsunaga, Shigeki ; Lin, Luqing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3035-8dacf2df63d194367c95b2e4af9fe7147304246f2d27c220416c0e681ee37b473</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aromatic compounds</topic><topic>Biological Products</topic><topic>Bromides</topic><topic>Carbon</topic><topic>Carbon - chemistry</topic><topic>carbon–heteroatom bonds</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Couplings</topic><topic>cross-coupling</topic><topic>Functional groups</topic><topic>Iodides</topic><topic>Natural products</topic><topic>Nickel</topic><topic>Nickel - chemistry</topic><topic>nickel catalysis</topic><topic>Nucleophiles</topic><topic>Oxygen - chemistry</topic><topic>reductive elimination</topic><topic>Sulfur</topic><topic>visible-light</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Luo, Hang</creatorcontrib><creatorcontrib>Wang, Guohua</creatorcontrib><creatorcontrib>Feng, Yunhui</creatorcontrib><creatorcontrib>Zheng, Wanyao</creatorcontrib><creatorcontrib>Kong, Lingya</creatorcontrib><creatorcontrib>Ma, Yunpeng</creatorcontrib><creatorcontrib>Matsunaga, Shigeki</creatorcontrib><creatorcontrib>Lin, Luqing</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Luo, Hang</au><au>Wang, Guohua</au><au>Feng, Yunhui</au><au>Zheng, Wanyao</au><au>Kong, Lingya</au><au>Ma, Yunpeng</au><au>Matsunaga, Shigeki</au><au>Lin, Luqing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photoinduced Nickel‐Catalyzed Carbon–Heteroatom Coupling</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2023-01-02</date><risdate>2023</risdate><volume>29</volume><issue>1</issue><spage>e202202385</spage><epage>n/a</epage><pages>e202202385-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Herein, we report visible light‐promoted single nickel catalysis for diverse carbon–heteroatom couplings under mild conditions. This mild, general, and robust method to couple diverse nitrogen, oxygen, and sulfur nucleophiles with aryl(heteroaryl)/alkenyl iodides/bromides exhibits a wide functional group tolerance and is applicable to late‐stage modification of pharmaceuticals and natural products. On the base of preliminary mechanistic studies, a NiI/NiIII cycle via the generation of active NiI complexes that appear from homolysis of NiII−I rather than NiII−aryl bond was tentatively proposed.
Exogenous photocatalyst‐free, single nickel‐catalyzed carbon–heteroatom coupling under visible‐light irradiation is reported. Over 15 classes of nucleophile can efficiently couple with aryl/alkene halides to afford valuable heteroatomic arenes/alkenes. The unprecedentedly broad substrate scope and late‐stage modification of valuable molecules fully demonstrate the benefits of the method.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36214656</pmid><doi>10.1002/chem.202202385</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-4738-0886</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2023-01, Vol.29 (1), p.e202202385-n/a |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2723485763 |
| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Aromatic compounds Biological Products Bromides Carbon Carbon - chemistry carbon–heteroatom bonds Catalysis Chemistry Couplings cross-coupling Functional groups Iodides Natural products Nickel Nickel - chemistry nickel catalysis Nucleophiles Oxygen - chemistry reductive elimination Sulfur visible-light |
| title | Photoinduced Nickel‐Catalyzed Carbon–Heteroatom Coupling |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T12%3A35%3A44IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Photoinduced%20Nickel%E2%80%90Catalyzed%20Carbon%E2%80%93Heteroatom%20Coupling&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Luo,%20Hang&rft.date=2023-01-02&rft.volume=29&rft.issue=1&rft.spage=e202202385&rft.epage=n/a&rft.pages=e202202385-n/a&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.202202385&rft_dat=%3Cproquest_cross%3E2723485763%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2773745591&rft_id=info:pmid/36214656&rfr_iscdi=true |