A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups
A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para‐, meta‐, and ortho‐positions. Alkyl p‐ and m‐lithiobenzoates were generated by the I/Li exchange reaction wi...
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| Veröffentlicht in: | Chemistry : a European journal 2010-09, Vol.16 (36), p.11167-11177 |
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| container_end_page | 11177 |
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| container_issue | 36 |
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| container_title | Chemistry : a European journal |
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| creator | Nagaki, Aiichiro Kim, Heejin Moriwaki, Yuya Matsuo, Chika Yoshida, Jun-ichi |
| description | A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para‐, meta‐, and ortho‐positions. Alkyl p‐ and m‐lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o‐lithiobenzoates were successfully generated by the Br/Li exchange reaction with sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.
Go micro! A flow microreactor system serves as a straightforward method for the generation and reaction of aryllithium compounds bearing an alkoxycarbonyl group (see scheme). |
| doi_str_mv | 10.1002/chem.201000876 |
| format | Article |
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Go micro! A flow microreactor system serves as a straightforward method for the generation and reaction of aryllithium compounds bearing an alkoxycarbonyl group (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201000876</identifier><identifier>PMID: 20715202</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>aryllithium ; Bearing ; Exchange ; flash chemistry ; Lithium ; Microreactors ; organometallic compounds ; protecting groups ; Reactors</subject><ispartof>Chemistry : a European journal, 2010-09, Vol.16 (36), p.11167-11177</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5096-d534d6622608fd04391db235e4771931e929d01854a25e3bc86e140fa2f112653</citedby><cites>FETCH-LOGICAL-c5096-d534d6622608fd04391db235e4771931e929d01854a25e3bc86e140fa2f112653</cites></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.201000876$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201000876$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20715202$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nagaki, Aiichiro</creatorcontrib><creatorcontrib>Kim, Heejin</creatorcontrib><creatorcontrib>Moriwaki, Yuya</creatorcontrib><creatorcontrib>Matsuo, Chika</creatorcontrib><creatorcontrib>Yoshida, Jun-ichi</creatorcontrib><title>A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups</title><title>Chemistry : a European journal</title><addtitle>Chemistry - A European Journal</addtitle><description>A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para‐, meta‐, and ortho‐positions. Alkyl p‐ and m‐lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o‐lithiobenzoates were successfully generated by the Br/Li exchange reaction with sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.
Go micro! A flow microreactor system serves as a straightforward method for the generation and reaction of aryllithium compounds bearing an alkoxycarbonyl group (see scheme).</description><subject>aryllithium</subject><subject>Bearing</subject><subject>Exchange</subject><subject>flash chemistry</subject><subject>Lithium</subject><subject>Microreactors</subject><subject>organometallic compounds</subject><subject>protecting groups</subject><subject>Reactors</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqF0c9v0zAUB3ALgVgZXDkiSxzgkuIfsR0fq6rrQB3jp8bNchJny-bExU7U5b_nVR0V4gAnW9bnPfm9L0IvKZlTQti76sZ1c0bgTgolH6EZFYxmXEnxGM2IzlUmBdcn6FlKt2C05PwpOmFEgSNshqoFPvNhhy_aKobobDWEiL9OaXAdXvW29C7hy3ht--Db4aYdO_xlj9rQJ7yDlzAO-FMMg4O3_hov_F24nyoby9BPHq9jGLfpOXrSWJ_ci4fzFH0_W31bnmeby_X75WKTVQI-ltWC57WUjElSNDXJuaZ1ybhwuVJUc-o00zWhhcgtE46XVSEdzUljWUMpgzFP0ZtD320MP0eXBtO1qXLe296FMRklYBVaUgry7T8lVaogVPCiAPr6L3obxtjDHKCkFFrkmoGaHxRsMaXoGrONbWfjZCgx-6DMPihzDAoKXj20HcvO1Uf-OxkA-gB2rXfTf9qZ5fnq4s_m2aG2hRzvj7U23hmpuBLm6uPafNjkklytf5jP_BeaxK1K</recordid><startdate>20100924</startdate><enddate>20100924</enddate><creator>Nagaki, Aiichiro</creator><creator>Kim, Heejin</creator><creator>Moriwaki, Yuya</creator><creator>Matsuo, Chika</creator><creator>Yoshida, Jun-ichi</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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></search><sort><creationdate>20100924</creationdate><title>A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups</title><author>Nagaki, Aiichiro ; Kim, Heejin ; Moriwaki, Yuya ; Matsuo, Chika ; Yoshida, Jun-ichi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5096-d534d6622608fd04391db235e4771931e929d01854a25e3bc86e140fa2f112653</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>aryllithium</topic><topic>Bearing</topic><topic>Exchange</topic><topic>flash chemistry</topic><topic>Lithium</topic><topic>Microreactors</topic><topic>organometallic compounds</topic><topic>protecting groups</topic><topic>Reactors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nagaki, Aiichiro</creatorcontrib><creatorcontrib>Kim, Heejin</creatorcontrib><creatorcontrib>Moriwaki, Yuya</creatorcontrib><creatorcontrib>Matsuo, Chika</creatorcontrib><creatorcontrib>Yoshida, Jun-ichi</creatorcontrib><collection>Istex</collection><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>Nagaki, Aiichiro</au><au>Kim, Heejin</au><au>Moriwaki, Yuya</au><au>Matsuo, Chika</au><au>Yoshida, Jun-ichi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry - A European Journal</addtitle><date>2010-09-24</date><risdate>2010</risdate><volume>16</volume><issue>36</issue><spage>11167</spage><epage>11177</epage><pages>11167-11177</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para‐, meta‐, and ortho‐positions. Alkyl p‐ and m‐lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o‐lithiobenzoates were successfully generated by the Br/Li exchange reaction with sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | aryllithium Bearing Exchange flash chemistry Lithium Microreactors organometallic compounds protecting groups Reactors |
| title | A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups |
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