Copper‐Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates
A copper‐catalyzed trifunctionalization of alkynes that provides rapid access to oxindoles bearing a geminal diboronate side chain, highlighted by the simultaneous formation of one C−C bond and two C−B bonds, is reported. This new reaction features simple reaction conditions (ligand‐free catalysis),...
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| Veröffentlicht in: | Chemistry : a European journal 2019-01, Vol.25 (4), p.966-970 |
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| container_issue | 4 |
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| container_title | Chemistry : a European journal |
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| creator | He, Tao Li, Bin Liu, Li‐Chuan Wang, Jing Ma, Wen‐Peng Li, Guang‐Yu Zhang, Qing‐Wei He, Wei |
| description | A copper‐catalyzed trifunctionalization of alkynes that provides rapid access to oxindoles bearing a geminal diboronate side chain, highlighted by the simultaneous formation of one C−C bond and two C−B bonds, is reported. This new reaction features simple reaction conditions (ligand‐free catalysis), a general substrate scope, and excellent chemoselectivity. Mechanistic study revealed a reaction sequence constituted by, in the order, borylation, intramolecular cross‐coupling, hydroboration, which has been rarely documented.
A ligand‐free CuI‐catalyzed trifunctionalization of 2‐ynamide was developed, which provides rapid access to oxindoles bearing a geminal diboronate substitution on the side chain. The new reaction features simple reaction conditions, a general substrate scope and excellent chemoselectivity. |
| doi_str_mv | 10.1002/chem.201804480 |
| format | Article |
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A ligand‐free CuI‐catalyzed trifunctionalization of 2‐ynamide was developed, which provides rapid access to oxindoles bearing a geminal diboronate substitution on the side chain. The new reaction features simple reaction conditions, a general substrate scope and excellent chemoselectivity.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201804480</identifier><identifier>PMID: 30324715</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Bearing ; bis-borylation ; Catalysis ; Chemistry ; Copper ; Hydroboration ; oxindoles ; Substrates ; trifunctionalization</subject><ispartof>Chemistry : a European journal, 2019-01, Vol.25 (4), p.966-970</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4100-44982ccce60ac630accce0cb2ef868109bbdebb196ee3f55c38890fe25933d243</citedby><cites>FETCH-LOGICAL-c4100-44982ccce60ac630accce0cb2ef868109bbdebb196ee3f55c38890fe25933d243</cites><orcidid>0000-0001-8167-9155</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.201804480$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201804480$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30324715$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>He, Tao</creatorcontrib><creatorcontrib>Li, Bin</creatorcontrib><creatorcontrib>Liu, Li‐Chuan</creatorcontrib><creatorcontrib>Wang, Jing</creatorcontrib><creatorcontrib>Ma, Wen‐Peng</creatorcontrib><creatorcontrib>Li, Guang‐Yu</creatorcontrib><creatorcontrib>Zhang, Qing‐Wei</creatorcontrib><creatorcontrib>He, Wei</creatorcontrib><title>Copper‐Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A copper‐catalyzed trifunctionalization of alkynes that provides rapid access to oxindoles bearing a geminal diboronate side chain, highlighted by the simultaneous formation of one C−C bond and two C−B bonds, is reported. This new reaction features simple reaction conditions (ligand‐free catalysis), a general substrate scope, and excellent chemoselectivity. Mechanistic study revealed a reaction sequence constituted by, in the order, borylation, intramolecular cross‐coupling, hydroboration, which has been rarely documented.
A ligand‐free CuI‐catalyzed trifunctionalization of 2‐ynamide was developed, which provides rapid access to oxindoles bearing a geminal diboronate substitution on the side chain. The new reaction features simple reaction conditions, a general substrate scope and excellent chemoselectivity.</description><subject>Alkynes</subject><subject>Bearing</subject><subject>bis-borylation</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Copper</subject><subject>Hydroboration</subject><subject>oxindoles</subject><subject>Substrates</subject><subject>trifunctionalization</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkc9O3DAQhy3UCra0V45VpF64ZDu24yTuDVL-SSCkip4jx5lQUydO7Y3ocuoj9Bn7JDha2EpcuNgjzTef7PkRckBhSQHYZ_0D-yUDWkKWlbBDFlQwmvIiF2_IAmRWpLngco-8C-EOAGTO-S7Z48BZVlCxILZy44j-35-_lVopu37ANrnxppsGvTJuUNY8qLlIXJcc2Z_rAcOX5JsaTZucOt9ve9e_zdA6iyE5RuXNcJucYW_ifPLVNM5H0wrDe_K2Uzbgh6d7n3w_PbmpztPL67OL6ugy1Vn8VJplsmRaa8xB6ZzHI9agG4ZdmZcUZNO02DRU5oi8E0LzspTQIROS85ZlfJ8cbryjd78mDKu6N0GjtWpAN4WaUQaFEMCKiH56gd65ycd3z1QuGXAqZuFyQ2nvQvDY1aM3vfLrmkI951DPOdTbHOLAxyft1PTYbvHnxUdAboB7Y3H9iq6uzk-u_ssfAR8xlm8</recordid><startdate>20190118</startdate><enddate>20190118</enddate><creator>He, Tao</creator><creator>Li, Bin</creator><creator>Liu, Li‐Chuan</creator><creator>Wang, Jing</creator><creator>Ma, Wen‐Peng</creator><creator>Li, Guang‐Yu</creator><creator>Zhang, Qing‐Wei</creator><creator>He, Wei</creator><general>Wiley Subscription Services, Inc</general><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/0000-0001-8167-9155</orcidid></search><sort><creationdate>20190118</creationdate><title>Copper‐Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates</title><author>He, Tao ; Li, Bin ; Liu, Li‐Chuan ; Wang, Jing ; Ma, Wen‐Peng ; Li, Guang‐Yu ; Zhang, Qing‐Wei ; He, Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4100-44982ccce60ac630accce0cb2ef868109bbdebb196ee3f55c38890fe25933d243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkynes</topic><topic>Bearing</topic><topic>bis-borylation</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Copper</topic><topic>Hydroboration</topic><topic>oxindoles</topic><topic>Substrates</topic><topic>trifunctionalization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Tao</creatorcontrib><creatorcontrib>Li, Bin</creatorcontrib><creatorcontrib>Liu, Li‐Chuan</creatorcontrib><creatorcontrib>Wang, Jing</creatorcontrib><creatorcontrib>Ma, Wen‐Peng</creatorcontrib><creatorcontrib>Li, Guang‐Yu</creatorcontrib><creatorcontrib>Zhang, Qing‐Wei</creatorcontrib><creatorcontrib>He, Wei</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>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>He, Tao</au><au>Li, Bin</au><au>Liu, Li‐Chuan</au><au>Wang, Jing</au><au>Ma, Wen‐Peng</au><au>Li, Guang‐Yu</au><au>Zhang, Qing‐Wei</au><au>He, Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper‐Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2019-01-18</date><risdate>2019</risdate><volume>25</volume><issue>4</issue><spage>966</spage><epage>970</epage><pages>966-970</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A copper‐catalyzed trifunctionalization of alkynes that provides rapid access to oxindoles bearing a geminal diboronate side chain, highlighted by the simultaneous formation of one C−C bond and two C−B bonds, is reported. This new reaction features simple reaction conditions (ligand‐free catalysis), a general substrate scope, and excellent chemoselectivity. Mechanistic study revealed a reaction sequence constituted by, in the order, borylation, intramolecular cross‐coupling, hydroboration, which has been rarely documented.
A ligand‐free CuI‐catalyzed trifunctionalization of 2‐ynamide was developed, which provides rapid access to oxindoles bearing a geminal diboronate substitution on the side chain. The new reaction features simple reaction conditions, a general substrate scope and excellent chemoselectivity.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30324715</pmid><doi>10.1002/chem.201804480</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-8167-9155</orcidid></addata></record> |
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| subjects | Alkynes Bearing bis-borylation Catalysis Chemistry Copper Hydroboration oxindoles Substrates trifunctionalization |
| title | Copper‐Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates |
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