Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C−H Activation/Alkyne Insertion Reaction
A nickel/NHC system for regioselective oxidative annulation by double C−H bond activation and concomitant alkyne insertion is described. The catalytic reaction requires a bidentate directing group, such as an 8‐aminoquinoline, embedded in the substrate. Various 5,6,7,8‐tetrasubstituted‐N‐(quinolin‐8...
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| Veröffentlicht in: | Chemistry : a European journal 2016-01, Vol.22 (4), p.1362-1367 |
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| container_title | Chemistry : a European journal |
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| creator | Misal Castro, Luis C. Obata, Atsushi Aihara, Yoshinori Chatani, Naoto |
| description | A nickel/NHC system for regioselective oxidative annulation by double C−H bond activation and concomitant alkyne insertion is described. The catalytic reaction requires a bidentate directing group, such as an 8‐aminoquinoline, embedded in the substrate. Various 5,6,7,8‐tetrasubstituted‐N‐(quinolin‐8‐yl)‐1‐naphthamides can be prepared as well as phenanthrene and benzo[h]quinoline amide derivatives. Diarylalkynes, dialkylalkynes, and arylalkylalkynes can be used in the system. A Ni0/NiII catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor.
In two shakes: Oxidative annulation by a double C−H activation/alkyne insertion reaction was achieved by a nickel/NHC system. A Ni0/NiII catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor. |
| doi_str_mv | 10.1002/chem.201504596 |
| format | Article |
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In two shakes: Oxidative annulation by a double C−H activation/alkyne insertion reaction was achieved by a nickel/NHC system. A Ni0/NiII catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201504596</identifier><identifier>PMID: 26689750</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Activation ; Alkynes ; aromatic homologation ; Catalysis ; chelate-assistance ; Chelation ; Chemical bonds ; Chemical reactions ; Chemistry ; Coupling ; C−H activation ; Derivatives ; Hydrogen ; Insertion ; Nickel ; Organic chemistry ; Phenanthrene ; Quinoline</subject><ispartof>Chemistry : a European journal, 2016-01, Vol.22 (4), p.1362-1367</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5796-3b82c22484c2ec930cee8e34a11dfc6af97232dabc1e665033dda588fa5342783</citedby><cites>FETCH-LOGICAL-c5796-3b82c22484c2ec930cee8e34a11dfc6af97232dabc1e665033dda588fa5342783</cites></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.201504596$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201504596$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26689750$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Misal Castro, Luis C.</creatorcontrib><creatorcontrib>Obata, Atsushi</creatorcontrib><creatorcontrib>Aihara, Yoshinori</creatorcontrib><creatorcontrib>Chatani, Naoto</creatorcontrib><title>Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C−H Activation/Alkyne Insertion Reaction</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A nickel/NHC system for regioselective oxidative annulation by double C−H bond activation and concomitant alkyne insertion is described. The catalytic reaction requires a bidentate directing group, such as an 8‐aminoquinoline, embedded in the substrate. Various 5,6,7,8‐tetrasubstituted‐N‐(quinolin‐8‐yl)‐1‐naphthamides can be prepared as well as phenanthrene and benzo[h]quinoline amide derivatives. Diarylalkynes, dialkylalkynes, and arylalkylalkynes can be used in the system. A Ni0/NiII catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor.
In two shakes: Oxidative annulation by a double C−H activation/alkyne insertion reaction was achieved by a nickel/NHC system. A Ni0/NiII catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor.</description><subject>Activation</subject><subject>Alkynes</subject><subject>aromatic homologation</subject><subject>Catalysis</subject><subject>chelate-assistance</subject><subject>Chelation</subject><subject>Chemical bonds</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Coupling</subject><subject>C−H activation</subject><subject>Derivatives</subject><subject>Hydrogen</subject><subject>Insertion</subject><subject>Nickel</subject><subject>Organic chemistry</subject><subject>Phenanthrene</subject><subject>Quinoline</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqF0c1O3DAUBWALtYIpsGVZReo6w7Ud_y3TFAgSBQlBy87yODciTCah8QSYPkHXfcQ-STMERqzalS37u8eSDyEHFKYUgB36W1xMGVABiTByi0yoYDTmSop3ZAImUbEU3OyQDyHcAYCRnG-THSalNkrAhDTZLdZuWbVNnIZQhSUW0Xnl51jHmVu6evVzOLh4qorBPGCUNk0_8uihctGXtp_VGGV_fv3Oo9QP5PnuMK3nqwaj0yZg94wv0fn1Zo-8L10dcP9l3SXXx0dXWR6fXZycZulZ7IUyMuYzzTxjiU48Q284eESNPHGUFqWXrjSKcVa4macopQDOi8IJrUsneMKU5rvk05h737U_egxLe9f2XTM8aakBxbTWSv1TKSGBiQTMoKaj8l0bQoelve-qhetWloJdl2DXJdhNCcPAx5fYfrbAYsNff30AZgSPVY2r_8TZLD_6-jY8HmfXXT1tZl03t1JxJez38xMLOc9vzNU3-5n_BQeao3o</recordid><startdate>20160122</startdate><enddate>20160122</enddate><creator>Misal Castro, Luis C.</creator><creator>Obata, Atsushi</creator><creator>Aihara, Yoshinori</creator><creator>Chatani, Naoto</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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></search><sort><creationdate>20160122</creationdate><title>Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C−H Activation/Alkyne Insertion Reaction</title><author>Misal Castro, Luis C. ; Obata, Atsushi ; Aihara, Yoshinori ; Chatani, Naoto</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5796-3b82c22484c2ec930cee8e34a11dfc6af97232dabc1e665033dda588fa5342783</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Activation</topic><topic>Alkynes</topic><topic>aromatic homologation</topic><topic>Catalysis</topic><topic>chelate-assistance</topic><topic>Chelation</topic><topic>Chemical bonds</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Coupling</topic><topic>C−H activation</topic><topic>Derivatives</topic><topic>Hydrogen</topic><topic>Insertion</topic><topic>Nickel</topic><topic>Organic chemistry</topic><topic>Phenanthrene</topic><topic>Quinoline</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Misal Castro, Luis C.</creatorcontrib><creatorcontrib>Obata, Atsushi</creatorcontrib><creatorcontrib>Aihara, Yoshinori</creatorcontrib><creatorcontrib>Chatani, Naoto</creatorcontrib><collection>Istex</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><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Misal Castro, Luis C.</au><au>Obata, Atsushi</au><au>Aihara, Yoshinori</au><au>Chatani, Naoto</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C−H Activation/Alkyne Insertion Reaction</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-01-22</date><risdate>2016</risdate><volume>22</volume><issue>4</issue><spage>1362</spage><epage>1367</epage><pages>1362-1367</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A nickel/NHC system for regioselective oxidative annulation by double C−H bond activation and concomitant alkyne insertion is described. The catalytic reaction requires a bidentate directing group, such as an 8‐aminoquinoline, embedded in the substrate. Various 5,6,7,8‐tetrasubstituted‐N‐(quinolin‐8‐yl)‐1‐naphthamides can be prepared as well as phenanthrene and benzo[h]quinoline amide derivatives. Diarylalkynes, dialkylalkynes, and arylalkylalkynes can be used in the system. A Ni0/NiII catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor.
In two shakes: Oxidative annulation by a double C−H activation/alkyne insertion reaction was achieved by a nickel/NHC system. A Ni0/NiII catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two‐component coupling partner and as a hydrogen acceptor.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26689750</pmid><doi>10.1002/chem.201504596</doi><tpages>6</tpages></addata></record> |
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| subjects | Activation Alkynes aromatic homologation Catalysis chelate-assistance Chelation Chemical bonds Chemical reactions Chemistry Coupling C−H activation Derivatives Hydrogen Insertion Nickel Organic chemistry Phenanthrene Quinoline |
| title | Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C−H Activation/Alkyne Insertion Reaction |
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