Controlled Reactivity of 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) in the Selective Synthesis of 1‐(Bromoethynyl)arenes
The nucleophilic reactivity of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) was completely controlled by the formation of monohydrate (DBU⋅H2O) in the synthesis of 1‐(bromoethynyl)arenes from 1,1‐dibromoalkenes. Differential reactivity of DBU in protic solvents as compared to aprotic solvents has been e...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2017-05, Vol.359 (9), p.1535-1540 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1540 |
|---|---|
| container_issue | 9 |
| container_start_page | 1535 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 359 |
| creator | Krishna Moodapelly, Shiva Sharma, Gangavaram V. M. Ramana Doddi, Venkata |
| description | The nucleophilic reactivity of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) was completely controlled by the formation of monohydrate (DBU⋅H2O) in the synthesis of 1‐(bromoethynyl)arenes from 1,1‐dibromoalkenes. Differential reactivity of DBU in protic solvents as compared to aprotic solvents has been explored to prevent the formation of mixtures of products in this reaction. Hydrated DBU is found to be superior to dry DBU, both for the selective synthesis and ease of isolation. In addition, use of DBU⋅H2O as a non‐nucleophilic mild base allowed us to synthesise 1‐(bromoethynyl)arenes via a reaction under solvent‐free conditions. Utilization of DBU⋅H2O as sole reagent also allowed us to isolate the products without column chromatographic purifications. |
| doi_str_mv | 10.1002/adsc.201601279 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1920432125</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1920432125</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4209-5085c3ea5ce4e479aa53291e828ad1e868c5edd7f62d6b86df37918ef9520a553</originalsourceid><addsrcrecordid>eNqFUE1Lw0AUDKJgrV49B7y0YOLuJptkj23qFxQEa08iy3b3haak2bqbKvEg_gR_o7_ErZV69PCY4b2ZeTCed4pRiBEiF0JZGRKEE4RJyva8Dk4wDWKcsP0dp-jQO7J2gRBOszTteO-5rhujqwqUfw9CNuVL2bS-Lnx8nn19fI5K8SZmpWxlpR9pGIfoaV0rkO6UuoEa_N5oOO37Ze03c_AnUMEmxLG2dgtb2p8wp-0NjV5qaOZt3VZ9YZzXHnsHhagsnPxi15teXT7kN8H47vo2H4wDGRPEAooyKiMQVEIMccqEoBFhGDKSCeUgySQFpdIiISqZZYkqopThDApGCRKURl3vbJu7Mvp5DbbhC702tXvJMSMojggmG1W4VUmjrTVQ8JUpl8K0HCO-6ZhvOua7jp2BbQ2vZQXtP2o-GE3yP-83_xKDVg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1920432125</pqid></control><display><type>article</type><title>Controlled Reactivity of 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) in the Selective Synthesis of 1‐(Bromoethynyl)arenes</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Krishna Moodapelly, Shiva ; Sharma, Gangavaram V. M. ; Ramana Doddi, Venkata</creator><creatorcontrib>Krishna Moodapelly, Shiva ; Sharma, Gangavaram V. M. ; Ramana Doddi, Venkata</creatorcontrib><description>The nucleophilic reactivity of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) was completely controlled by the formation of monohydrate (DBU⋅H2O) in the synthesis of 1‐(bromoethynyl)arenes from 1,1‐dibromoalkenes. Differential reactivity of DBU in protic solvents as compared to aprotic solvents has been explored to prevent the formation of mixtures of products in this reaction. Hydrated DBU is found to be superior to dry DBU, both for the selective synthesis and ease of isolation. In addition, use of DBU⋅H2O as a non‐nucleophilic mild base allowed us to synthesise 1‐(bromoethynyl)arenes via a reaction under solvent‐free conditions. Utilization of DBU⋅H2O as sole reagent also allowed us to isolate the products without column chromatographic purifications.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201601279</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>1,1-dibromoalkenes ; 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) ; 1-bromoalkynes ; alkynes ; Aromatic compounds ; controlled reactivity ; non-nucleophilic bases ; Reactivity ; Solvents ; Synthesis</subject><ispartof>Advanced synthesis & catalysis, 2017-05, Vol.359 (9), p.1535-1540</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4209-5085c3ea5ce4e479aa53291e828ad1e868c5edd7f62d6b86df37918ef9520a553</citedby><cites>FETCH-LOGICAL-c4209-5085c3ea5ce4e479aa53291e828ad1e868c5edd7f62d6b86df37918ef9520a553</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%2Fadsc.201601279$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201601279$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Krishna Moodapelly, Shiva</creatorcontrib><creatorcontrib>Sharma, Gangavaram V. M.</creatorcontrib><creatorcontrib>Ramana Doddi, Venkata</creatorcontrib><title>Controlled Reactivity of 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) in the Selective Synthesis of 1‐(Bromoethynyl)arenes</title><title>Advanced synthesis & catalysis</title><description>The nucleophilic reactivity of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) was completely controlled by the formation of monohydrate (DBU⋅H2O) in the synthesis of 1‐(bromoethynyl)arenes from 1,1‐dibromoalkenes. Differential reactivity of DBU in protic solvents as compared to aprotic solvents has been explored to prevent the formation of mixtures of products in this reaction. Hydrated DBU is found to be superior to dry DBU, both for the selective synthesis and ease of isolation. In addition, use of DBU⋅H2O as a non‐nucleophilic mild base allowed us to synthesise 1‐(bromoethynyl)arenes via a reaction under solvent‐free conditions. Utilization of DBU⋅H2O as sole reagent also allowed us to isolate the products without column chromatographic purifications.</description><subject>1,1-dibromoalkenes</subject><subject>1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)</subject><subject>1-bromoalkynes</subject><subject>alkynes</subject><subject>Aromatic compounds</subject><subject>controlled reactivity</subject><subject>non-nucleophilic bases</subject><subject>Reactivity</subject><subject>Solvents</subject><subject>Synthesis</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFUE1Lw0AUDKJgrV49B7y0YOLuJptkj23qFxQEa08iy3b3haak2bqbKvEg_gR_o7_ErZV69PCY4b2ZeTCed4pRiBEiF0JZGRKEE4RJyva8Dk4wDWKcsP0dp-jQO7J2gRBOszTteO-5rhujqwqUfw9CNuVL2bS-Lnx8nn19fI5K8SZmpWxlpR9pGIfoaV0rkO6UuoEa_N5oOO37Ze03c_AnUMEmxLG2dgtb2p8wp-0NjV5qaOZt3VZ9YZzXHnsHhagsnPxi15teXT7kN8H47vo2H4wDGRPEAooyKiMQVEIMccqEoBFhGDKSCeUgySQFpdIiISqZZYkqopThDApGCRKURl3vbJu7Mvp5DbbhC702tXvJMSMojggmG1W4VUmjrTVQ8JUpl8K0HCO-6ZhvOua7jp2BbQ2vZQXtP2o-GE3yP-83_xKDVg</recordid><startdate>20170502</startdate><enddate>20170502</enddate><creator>Krishna Moodapelly, Shiva</creator><creator>Sharma, Gangavaram V. M.</creator><creator>Ramana Doddi, Venkata</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20170502</creationdate><title>Controlled Reactivity of 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) in the Selective Synthesis of 1‐(Bromoethynyl)arenes</title><author>Krishna Moodapelly, Shiva ; Sharma, Gangavaram V. M. ; Ramana Doddi, Venkata</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4209-5085c3ea5ce4e479aa53291e828ad1e868c5edd7f62d6b86df37918ef9520a553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>1,1-dibromoalkenes</topic><topic>1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)</topic><topic>1-bromoalkynes</topic><topic>alkynes</topic><topic>Aromatic compounds</topic><topic>controlled reactivity</topic><topic>non-nucleophilic bases</topic><topic>Reactivity</topic><topic>Solvents</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krishna Moodapelly, Shiva</creatorcontrib><creatorcontrib>Sharma, Gangavaram V. M.</creatorcontrib><creatorcontrib>Ramana Doddi, Venkata</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krishna Moodapelly, Shiva</au><au>Sharma, Gangavaram V. M.</au><au>Ramana Doddi, Venkata</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Controlled Reactivity of 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) in the Selective Synthesis of 1‐(Bromoethynyl)arenes</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2017-05-02</date><risdate>2017</risdate><volume>359</volume><issue>9</issue><spage>1535</spage><epage>1540</epage><pages>1535-1540</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The nucleophilic reactivity of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) was completely controlled by the formation of monohydrate (DBU⋅H2O) in the synthesis of 1‐(bromoethynyl)arenes from 1,1‐dibromoalkenes. Differential reactivity of DBU in protic solvents as compared to aprotic solvents has been explored to prevent the formation of mixtures of products in this reaction. Hydrated DBU is found to be superior to dry DBU, both for the selective synthesis and ease of isolation. In addition, use of DBU⋅H2O as a non‐nucleophilic mild base allowed us to synthesise 1‐(bromoethynyl)arenes via a reaction under solvent‐free conditions. Utilization of DBU⋅H2O as sole reagent also allowed us to isolate the products without column chromatographic purifications.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201601279</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2017-05, Vol.359 (9), p.1535-1540 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_journals_1920432125 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 1,1-dibromoalkenes 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) 1-bromoalkynes alkynes Aromatic compounds controlled reactivity non-nucleophilic bases Reactivity Solvents Synthesis |
| title | Controlled Reactivity of 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) in the Selective Synthesis of 1‐(Bromoethynyl)arenes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-14T23%3A51%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Controlled%20Reactivity%20of%201,8%E2%80%90Diazabicyclo%5B5.4.0%5Dundec%E2%80%907%E2%80%90ene%20(DBU)%20in%20the%20Selective%20Synthesis%20of%201%E2%80%90(Bromoethynyl)arenes&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Krishna%E2%80%85Moodapelly,%20Shiva&rft.date=2017-05-02&rft.volume=359&rft.issue=9&rft.spage=1535&rft.epage=1540&rft.pages=1535-1540&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201601279&rft_dat=%3Cproquest_cross%3E1920432125%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1920432125&rft_id=info:pmid/&rfr_iscdi=true |