3,4,5-Trimethoxyphenyllithium
The 3,4,5-trimethoxypIieiiyl substituent is a frequently encountered substructure in a variety o f natural products. Therefore, it would be useful if this group could be introduced via a carbon-carbon bond forming reaction of the 3,4,5-trimethoxyphenyl carbanion and an appropriate carbon electro-phi...
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| Veröffentlicht in: | Synthetic communications 1982-01, Vol.12 (1), p.49-52 |
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| container_issue | 1 |
| container_start_page | 49 |
| container_title | Synthetic communications |
| container_volume | 12 |
| creator | Hoye, Thomas R. Kaese, Paul A. |
| description | The 3,4,5-trimethoxypIieiiyl substituent is a frequently encountered substructure in a variety o f natural products. Therefore, it would be useful if this group could be introduced via a carbon-carbon bond forming reaction of the 3,4,5-trimethoxyphenyl carbanion and an appropriate carbon electro-phile. We recently encountered a need to effect such a transformation and were surprised to learn of only a single report' regarding the preparation and use of thls anion. 3,4,5-Trimetlioxyphenyl bromide (1) was lithiated with E-butyllithium and carboxylated to generate 3,4,5-trimethoxybenzoic acid in 15% yield. In contrast 2,3,4-trimethoxyphenyl bromide has been lithiated and then methylated quite effiiently. We report here that the generation of 3,4,5-trimethoxyphenyllithium (2) from the bromide or iodide and Its subsequent addition to a variety of electrophiles is a straightforward and effective method for incorporation of this unit via C-C bond formation. |
| doi_str_mv | 10.1080/00397918208080065 |
| format | Article |
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Therefore, it would be useful if this group could be introduced via a carbon-carbon bond forming reaction of the 3,4,5-trimethoxyphenyl carbanion and an appropriate carbon electro-phile. We recently encountered a need to effect such a transformation and were surprised to learn of only a single report' regarding the preparation and use of thls anion. 3,4,5-Trimetlioxyphenyl bromide (1) was lithiated with E-butyllithium and carboxylated to generate 3,4,5-trimethoxybenzoic acid in 15% yield. In contrast 2,3,4-trimethoxyphenyl bromide has been lithiated and then methylated quite effiiently. We report here that the generation of 3,4,5-trimethoxyphenyllithium (2) from the bromide or iodide and Its subsequent addition to a variety of electrophiles is a straightforward and effective method for incorporation of this unit via C-C bond formation.</description><identifier>ISSN: 0039-7911</identifier><identifier>EISSN: 1532-2432</identifier><identifier>DOI: 10.1080/00397918208080065</identifier><language>eng</language><publisher>Taylor & Francis Group</publisher><ispartof>Synthetic communications, 1982-01, Vol.12 (1), p.49-52</ispartof><rights>Copyright Taylor & Francis Group, LLC 1982</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c296t-87df3f09129fa492a246bdf826bf54169e56051a306a8f389617df6a7bfe55403</citedby><cites>FETCH-LOGICAL-c296t-87df3f09129fa492a246bdf826bf54169e56051a306a8f389617df6a7bfe55403</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/00397918208080065$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/00397918208080065$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,776,780,27903,27904,59623,60412</link.rule.ids></links><search><creatorcontrib>Hoye, Thomas R.</creatorcontrib><creatorcontrib>Kaese, Paul A.</creatorcontrib><title>3,4,5-Trimethoxyphenyllithium</title><title>Synthetic communications</title><description>The 3,4,5-trimethoxypIieiiyl substituent is a frequently encountered substructure in a variety o f natural products. Therefore, it would be useful if this group could be introduced via a carbon-carbon bond forming reaction of the 3,4,5-trimethoxyphenyl carbanion and an appropriate carbon electro-phile. We recently encountered a need to effect such a transformation and were surprised to learn of only a single report' regarding the preparation and use of thls anion. 3,4,5-Trimetlioxyphenyl bromide (1) was lithiated with E-butyllithium and carboxylated to generate 3,4,5-trimethoxybenzoic acid in 15% yield. In contrast 2,3,4-trimethoxyphenyl bromide has been lithiated and then methylated quite effiiently. We report here that the generation of 3,4,5-trimethoxyphenyllithium (2) from the bromide or iodide and Its subsequent addition to a variety of electrophiles is a straightforward and effective method for incorporation of this unit via C-C bond formation.</description><issn>0039-7911</issn><issn>1532-2432</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1982</creationdate><recordtype>article</recordtype><recordid>eNp1j8tKBDEQRYMo2I5-gAv_YKJVeXUCbmTwBQNuxnVIdyd0pB9D0qL99_Yw7sRVcal7ijqEXCPcImi4A-CmNKjZEjSAkiekQMkZZYKzU1Ic9nQp4Dm5yPkDAGWpTUFu-FqsJd2l2PupHb_nfeuHuevi1MbP_pKcBddlf_U7V-T96XG3eaHbt-fXzcOW1syoieqyCTyAQWaCE4Y5JlTVBM1UFaRAZbxUINFxUE4Hro3ChVCurIKXUgBfETzerdOYc_LB7peHXJotgj342T9-C3N_ZOIQxtS7rzF1jZ3c3I0pJDfUMVv-P_4DSvhTTg</recordid><startdate>19820101</startdate><enddate>19820101</enddate><creator>Hoye, Thomas R.</creator><creator>Kaese, Paul A.</creator><general>Taylor & Francis Group</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19820101</creationdate><title>3,4,5-Trimethoxyphenyllithium</title><author>Hoye, Thomas R. ; Kaese, Paul A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-87df3f09129fa492a246bdf826bf54169e56051a306a8f389617df6a7bfe55403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1982</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hoye, Thomas R.</creatorcontrib><creatorcontrib>Kaese, Paul A.</creatorcontrib><collection>CrossRef</collection><jtitle>Synthetic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hoye, Thomas R.</au><au>Kaese, Paul A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>3,4,5-Trimethoxyphenyllithium</atitle><jtitle>Synthetic communications</jtitle><date>1982-01-01</date><risdate>1982</risdate><volume>12</volume><issue>1</issue><spage>49</spage><epage>52</epage><pages>49-52</pages><issn>0039-7911</issn><eissn>1532-2432</eissn><abstract>The 3,4,5-trimethoxypIieiiyl substituent is a frequently encountered substructure in a variety o f natural products. Therefore, it would be useful if this group could be introduced via a carbon-carbon bond forming reaction of the 3,4,5-trimethoxyphenyl carbanion and an appropriate carbon electro-phile. We recently encountered a need to effect such a transformation and were surprised to learn of only a single report' regarding the preparation and use of thls anion. 3,4,5-Trimetlioxyphenyl bromide (1) was lithiated with E-butyllithium and carboxylated to generate 3,4,5-trimethoxybenzoic acid in 15% yield. In contrast 2,3,4-trimethoxyphenyl bromide has been lithiated and then methylated quite effiiently. We report here that the generation of 3,4,5-trimethoxyphenyllithium (2) from the bromide or iodide and Its subsequent addition to a variety of electrophiles is a straightforward and effective method for incorporation of this unit via C-C bond formation.</abstract><pub>Taylor & Francis Group</pub><doi>10.1080/00397918208080065</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0039-7911 |
| ispartof | Synthetic communications, 1982-01, Vol.12 (1), p.49-52 |
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| source | Taylor & Francis Online |
| title | 3,4,5-Trimethoxyphenyllithium |
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