η3-Allyl Coordination at Tin(II)-Reactivity towards Alkynes and Benzonitrile
We herein report the synthesis and characterization of a terphenyl‐substituted SnII allyl compound featuring an η3 coordination mode in solution and in the solid state. Two examples for the interesting reactivity of the allyl SnII molecule are presented: Reactions with terminal alkynes result in the...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-04, Vol.54 (18), p.5502-5506 |
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| creator | Krebs, Kilian M. Wiederkehr, Jessica Schneider, Julia Schubert, Hartmut Eichele, Klaus Wesemann, Lars |
| description | We herein report the synthesis and characterization of a terphenyl‐substituted SnII allyl compound featuring an η3 coordination mode in solution and in the solid state. Two examples for the interesting reactivity of the allyl SnII molecule are presented: Reactions with terminal alkynes result in the formation of tricyclic compounds by CC bond formation and the dimerization of two Sn moieties whereas the reaction with benzonitrile leads to a sixteen‐membered ring system through CH activation.
3 to II: An example for the η3 coordination of an allyl group to a SnII center is presented. The allyl tin(II) compound undergoes allyl couplings in reactions with alkynes to yield tricyclic systems, and a sixteen‐membered macrocycle is formed with benzonitrile (see Scheme). |
| doi_str_mv | 10.1002/anie.201500386 |
| format | Article |
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3 to II: An example for the η3 coordination of an allyl group to a SnII center is presented. The allyl tin(II) compound undergoes allyl couplings in reactions with alkynes to yield tricyclic systems, and a sixteen‐membered macrocycle is formed with benzonitrile (see Scheme).</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201500386</identifier><language>eng ; jpn</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>alkynes ; allyl ligands ; macrocycles ; nitriles ; stannylene</subject><ispartof>Angewandte Chemie International Edition, 2015-04, Vol.54 (18), p.5502-5506</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201500386$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201500386$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27907,27908,45557,45558</link.rule.ids></links><search><creatorcontrib>Krebs, Kilian M.</creatorcontrib><creatorcontrib>Wiederkehr, Jessica</creatorcontrib><creatorcontrib>Schneider, Julia</creatorcontrib><creatorcontrib>Schubert, Hartmut</creatorcontrib><creatorcontrib>Eichele, Klaus</creatorcontrib><creatorcontrib>Wesemann, Lars</creatorcontrib><title>η3-Allyl Coordination at Tin(II)-Reactivity towards Alkynes and Benzonitrile</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>We herein report the synthesis and characterization of a terphenyl‐substituted SnII allyl compound featuring an η3 coordination mode in solution and in the solid state. Two examples for the interesting reactivity of the allyl SnII molecule are presented: Reactions with terminal alkynes result in the formation of tricyclic compounds by CC bond formation and the dimerization of two Sn moieties whereas the reaction with benzonitrile leads to a sixteen‐membered ring system through CH activation.
3 to II: An example for the η3 coordination of an allyl group to a SnII center is presented. The allyl tin(II) compound undergoes allyl couplings in reactions with alkynes to yield tricyclic systems, and a sixteen‐membered macrocycle is formed with benzonitrile (see Scheme).</description><subject>alkynes</subject><subject>allyl ligands</subject><subject>macrocycles</subject><subject>nitriles</subject><subject>stannylene</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNo9kE1Pg0AQhjdGE2v16pmjHrbuB7vAEUk_MLWaWqO3zQBLshYXAxsr_jH_hb9JmhpOM5PM807mQeiSkgklhN2ANXrCCBWE8FAeoREVjGIeBPy4733OcRAKeorO2vat3w9DIkfo_veH47iquspL6ropjAVnauuB8zbGXqXpNV5ryJ35NK7zXL2Dpmi9uNp2Vrce2MK71fa7tsY1ptLn6KSEqtUX_3WMnmfTTbLAy4d5msRLbKjwJZYMJCFFRLIoBFFSkec5ZASgzAOQZZRJv2Q-REFWUhoJzZjsv-I6ApIxXwZ8jKJD7q4_2qmPxrxD0ylK1N6E2ptQgwkVr9LpMPUsPrCmdfprYKHZqj45EOplNVeL9Sx5fLp7VZz_AWLQZJU</recordid><startdate>20150427</startdate><enddate>20150427</enddate><creator>Krebs, Kilian M.</creator><creator>Wiederkehr, Jessica</creator><creator>Schneider, Julia</creator><creator>Schubert, Hartmut</creator><creator>Eichele, Klaus</creator><creator>Wesemann, Lars</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope></search><sort><creationdate>20150427</creationdate><title>η3-Allyl Coordination at Tin(II)-Reactivity towards Alkynes and Benzonitrile</title><author>Krebs, Kilian M. ; Wiederkehr, Jessica ; Schneider, Julia ; Schubert, Hartmut ; Eichele, Klaus ; Wesemann, Lars</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i1546-62a600d90b98a5f15cccab0aafc7a6f9b64f24a97bf1195e2261503e9a0b24673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; jpn</language><creationdate>2015</creationdate><topic>alkynes</topic><topic>allyl ligands</topic><topic>macrocycles</topic><topic>nitriles</topic><topic>stannylene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krebs, Kilian M.</creatorcontrib><creatorcontrib>Wiederkehr, Jessica</creatorcontrib><creatorcontrib>Schneider, Julia</creatorcontrib><creatorcontrib>Schubert, Hartmut</creatorcontrib><creatorcontrib>Eichele, Klaus</creatorcontrib><creatorcontrib>Wesemann, Lars</creatorcontrib><collection>Istex</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krebs, Kilian M.</au><au>Wiederkehr, Jessica</au><au>Schneider, Julia</au><au>Schubert, Hartmut</au><au>Eichele, Klaus</au><au>Wesemann, Lars</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>η3-Allyl Coordination at Tin(II)-Reactivity towards Alkynes and Benzonitrile</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-04-27</date><risdate>2015</risdate><volume>54</volume><issue>18</issue><spage>5502</spage><epage>5506</epage><pages>5502-5506</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>We herein report the synthesis and characterization of a terphenyl‐substituted SnII allyl compound featuring an η3 coordination mode in solution and in the solid state. Two examples for the interesting reactivity of the allyl SnII molecule are presented: Reactions with terminal alkynes result in the formation of tricyclic compounds by CC bond formation and the dimerization of two Sn moieties whereas the reaction with benzonitrile leads to a sixteen‐membered ring system through CH activation.
3 to II: An example for the η3 coordination of an allyl group to a SnII center is presented. The allyl tin(II) compound undergoes allyl couplings in reactions with alkynes to yield tricyclic systems, and a sixteen‐membered macrocycle is formed with benzonitrile (see Scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/anie.201500386</doi><tpages>5</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | alkynes allyl ligands macrocycles nitriles stannylene |
| title | η3-Allyl Coordination at Tin(II)-Reactivity towards Alkynes and Benzonitrile |
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