Microwave-Assisted Efficient One-Pot Synthesis of 9‑Phenyl-9,10-disilatriptycene and Its Bridgehead Functionalization
9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disilaanthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was signif...
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| Veröffentlicht in: | Organometallics 2013-04, Vol.32 (7), p.2092-2098 |
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| container_title | Organometallics |
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| creator | Kuribara, Takayoshi Ishida, Shintaro Kudo, Takako Kyushin, Soichiro |
| description | 9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disilaanthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was significantly increased to 71% on microwave irradiation. Theoretical calculations suggest that the intermediary Grignard reagents generated from trans- and cis-9,10-diaryl-9,10-dihydro-9,10-disilaanthracenes have quite different reactivity for construction of the 9,10-disilatriptycene skeleton. The bridgehead Si–H moiety of 2 was readily functionalized to give several 9,10-disilatriptycene derivatives. |
| doi_str_mv | 10.1021/om301170r |
| format | Article |
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On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disilaanthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was significantly increased to 71% on microwave irradiation. Theoretical calculations suggest that the intermediary Grignard reagents generated from trans- and cis-9,10-diaryl-9,10-dihydro-9,10-disilaanthracenes have quite different reactivity for construction of the 9,10-disilatriptycene skeleton. The bridgehead Si–H moiety of 2 was readily functionalized to give several 9,10-disilatriptycene derivatives.</description><identifier>ISSN: 0276-7333</identifier><identifier>EISSN: 1520-6041</identifier><identifier>DOI: 10.1021/om301170r</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organometallics, 2013-04, Vol.32 (7), p.2092-2098</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a325t-1d4e5a49b628338c68c18b616d6b535e5c00dc907ba0ad598c9d122eae2f46383</citedby><cites>FETCH-LOGICAL-a325t-1d4e5a49b628338c68c18b616d6b535e5c00dc907ba0ad598c9d122eae2f46383</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/om301170r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/om301170r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Kuribara, Takayoshi</creatorcontrib><creatorcontrib>Ishida, Shintaro</creatorcontrib><creatorcontrib>Kudo, Takako</creatorcontrib><creatorcontrib>Kyushin, Soichiro</creatorcontrib><title>Microwave-Assisted Efficient One-Pot Synthesis of 9‑Phenyl-9,10-disilatriptycene and Its Bridgehead Functionalization</title><title>Organometallics</title><addtitle>Organometallics</addtitle><description>9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disilaanthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was significantly increased to 71% on microwave irradiation. Theoretical calculations suggest that the intermediary Grignard reagents generated from trans- and cis-9,10-diaryl-9,10-dihydro-9,10-disilaanthracenes have quite different reactivity for construction of the 9,10-disilatriptycene skeleton. The bridgehead Si–H moiety of 2 was readily functionalized to give several 9,10-disilatriptycene derivatives.</description><issn>0276-7333</issn><issn>1520-6041</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNptkM1KAzEUhYMoWKsL3yAbF4LR_MxkZpa1tFqotKCuh0xyx6a0mZKklnHlK_iKPolTKq5cnQPn43DvQeiS0VtGObtr1oIyllF_hHos5ZRImrBj1KM8kyQTQpyisxCWlFKZCd5DuyerfbNT70AGIdgQweBRXVttwUU8c0DmTcTPrYsL6GLc1Lj4_vyaL8C1K1LcMEqMDXaloreb2GpwgJUzeBIDvvfWvMEClMHjrdPRNk6t7Ifam3N0UqtVgItf7aPX8ehl-Eims4fJcDAlSvA0EmYSSFVSVJLnQuRa5prllWTSyCoVKaSaUqMLmlWKKpMWuS4M4xwU8DqRIhd9dH3o7b4MwUNdbrxdK9-WjJb7xcq_xTr26sAqHcpls_XdueEf7gdwPGxk</recordid><startdate>20130408</startdate><enddate>20130408</enddate><creator>Kuribara, Takayoshi</creator><creator>Ishida, Shintaro</creator><creator>Kudo, Takako</creator><creator>Kyushin, Soichiro</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130408</creationdate><title>Microwave-Assisted Efficient One-Pot Synthesis of 9‑Phenyl-9,10-disilatriptycene and Its Bridgehead Functionalization</title><author>Kuribara, Takayoshi ; Ishida, Shintaro ; Kudo, Takako ; Kyushin, Soichiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a325t-1d4e5a49b628338c68c18b616d6b535e5c00dc907ba0ad598c9d122eae2f46383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuribara, Takayoshi</creatorcontrib><creatorcontrib>Ishida, Shintaro</creatorcontrib><creatorcontrib>Kudo, Takako</creatorcontrib><creatorcontrib>Kyushin, Soichiro</creatorcontrib><collection>CrossRef</collection><jtitle>Organometallics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kuribara, Takayoshi</au><au>Ishida, Shintaro</au><au>Kudo, Takako</au><au>Kyushin, Soichiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-Assisted Efficient One-Pot Synthesis of 9‑Phenyl-9,10-disilatriptycene and Its Bridgehead Functionalization</atitle><jtitle>Organometallics</jtitle><addtitle>Organometallics</addtitle><date>2013-04-08</date><risdate>2013</risdate><volume>32</volume><issue>7</issue><spage>2092</spage><epage>2098</epage><pages>2092-2098</pages><issn>0276-7333</issn><eissn>1520-6041</eissn><abstract>9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disilaanthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was significantly increased to 71% on microwave irradiation. Theoretical calculations suggest that the intermediary Grignard reagents generated from trans- and cis-9,10-diaryl-9,10-dihydro-9,10-disilaanthracenes have quite different reactivity for construction of the 9,10-disilatriptycene skeleton. The bridgehead Si–H moiety of 2 was readily functionalized to give several 9,10-disilatriptycene derivatives.</abstract><pub>American Chemical Society</pub><doi>10.1021/om301170r</doi><tpages>7</tpages></addata></record> |
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| title | Microwave-Assisted Efficient One-Pot Synthesis of 9‑Phenyl-9,10-disilatriptycene and Its Bridgehead Functionalization |
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