Copper catalyzed Heck-like cyclizations of oxime esters
Copper catalyzed Heck-like cyclizations of oxime esters are described. Mechanistic studies indicate a reaction pathway that proceeds via the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples o...
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| Veröffentlicht in: | Chemical science (Cambridge) 2014-01, Vol.5 (6), p.2416-2421 |
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| container_title | Chemical science (Cambridge) |
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| creator | Faulkner, Adele Race, Nicholas J. Scott, James S. Bower, John F. |
| description | Copper catalyzed Heck-like cyclizations of oxime esters are described. Mechanistic studies indicate a reaction pathway that proceeds
via
the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples of Cu-catalyzed aza-Heck reactions that proceed
via
oxidative initiation at nitrogen to generate products containing a new alkene. This new protocol is also an effective alternative to Pd-based systems and highlights the value of replacing precious metal catalysts with cheaper and more sustainable variants. |
| doi_str_mv | 10.1039/C4SC00652F |
| format | Article |
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via
the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples of Cu-catalyzed aza-Heck reactions that proceed
via
oxidative initiation at nitrogen to generate products containing a new alkene. This new protocol is also an effective alternative to Pd-based systems and highlights the value of replacing precious metal catalysts with cheaper and more sustainable variants.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/C4SC00652F</identifier><language>eng</language><subject>Catalysis ; Copper ; Esters ; Olefins ; Oximes ; Precious metals ; Radicals ; Sustainability</subject><ispartof>Chemical science (Cambridge), 2014-01, Vol.5 (6), p.2416-2421</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c366t-c54d537090afd6240572c8c7b0a0c087cdf22f3636bb39ba939ef75f98585f5f3</citedby><cites>FETCH-LOGICAL-c366t-c54d537090afd6240572c8c7b0a0c087cdf22f3636bb39ba939ef75f98585f5f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Faulkner, Adele</creatorcontrib><creatorcontrib>Race, Nicholas J.</creatorcontrib><creatorcontrib>Scott, James S.</creatorcontrib><creatorcontrib>Bower, John F.</creatorcontrib><title>Copper catalyzed Heck-like cyclizations of oxime esters</title><title>Chemical science (Cambridge)</title><description>Copper catalyzed Heck-like cyclizations of oxime esters are described. Mechanistic studies indicate a reaction pathway that proceeds
via
the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples of Cu-catalyzed aza-Heck reactions that proceed
via
oxidative initiation at nitrogen to generate products containing a new alkene. This new protocol is also an effective alternative to Pd-based systems and highlights the value of replacing precious metal catalysts with cheaper and more sustainable variants.</description><subject>Catalysis</subject><subject>Copper</subject><subject>Esters</subject><subject>Olefins</subject><subject>Oximes</subject><subject>Precious metals</subject><subject>Radicals</subject><subject>Sustainability</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpFkEFLxDAUhIMouKx78Rf0KEL1Ja9JmqMU1xUWPKjnkqYJxG03NemC3V9vZUXnMnP4mIEh5JrCHQVU91XxWgEIztZnZMGgoLngqM7_MoNLskrpA2YhUs7kgsgqDIONmdGj7qajbbONNbu88zubmcl0_qhHH_YpCy4LX763mU2jjemKXDjdJbv69SV5Xz--VZt8-_L0XD1sc4NCjLnhRctRggLtWsEK4JKZ0sgGNBgopWkdYw4FiqZB1WiFyjrJnSp5yR13uCQ3p94hhs_DvF33PhnbdXpvwyHVVJaCCmSUzujtCTUxpBStq4foex2nmkL9c1D9fxB-A_L2Vr0</recordid><startdate>20140101</startdate><enddate>20140101</enddate><creator>Faulkner, Adele</creator><creator>Race, Nicholas J.</creator><creator>Scott, James S.</creator><creator>Bower, John F.</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140101</creationdate><title>Copper catalyzed Heck-like cyclizations of oxime esters</title><author>Faulkner, Adele ; Race, Nicholas J. ; Scott, James S. ; Bower, John F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c366t-c54d537090afd6240572c8c7b0a0c087cdf22f3636bb39ba939ef75f98585f5f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Catalysis</topic><topic>Copper</topic><topic>Esters</topic><topic>Olefins</topic><topic>Oximes</topic><topic>Precious metals</topic><topic>Radicals</topic><topic>Sustainability</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Faulkner, Adele</creatorcontrib><creatorcontrib>Race, Nicholas J.</creatorcontrib><creatorcontrib>Scott, James S.</creatorcontrib><creatorcontrib>Bower, John F.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Faulkner, Adele</au><au>Race, Nicholas J.</au><au>Scott, James S.</au><au>Bower, John F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper catalyzed Heck-like cyclizations of oxime esters</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2014-01-01</date><risdate>2014</risdate><volume>5</volume><issue>6</issue><spage>2416</spage><epage>2421</epage><pages>2416-2421</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Copper catalyzed Heck-like cyclizations of oxime esters are described. Mechanistic studies indicate a reaction pathway that proceeds
via
the generation and cyclization of an intermediate that possesses iminyl radical character. To the best of our knowledge, this work encompasses the first examples of Cu-catalyzed aza-Heck reactions that proceed
via
oxidative initiation at nitrogen to generate products containing a new alkene. This new protocol is also an effective alternative to Pd-based systems and highlights the value of replacing precious metal catalysts with cheaper and more sustainable variants.</abstract><doi>10.1039/C4SC00652F</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2014-01, Vol.5 (6), p.2416-2421 |
| issn | 2041-6520 2041-6539 |
| language | eng |
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| source | PubMed Central Open Access; Royal Society Of Chemistry Journals 2008-; PubMed Central |
| subjects | Catalysis Copper Esters Olefins Oximes Precious metals Radicals Sustainability |
| title | Copper catalyzed Heck-like cyclizations of oxime esters |
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