Facile synthesis of arylboronic esters by palladacycle-catalyzed bromination of 2-arylbenzoxazoles and subsequent borylation of the brominated products
An efficient and facile synthesis of arylboronic esters bearing the benzoxazole moiety has been described using a new family of palladacycle: cyclopalladated ferrocenylimines as the catalysts. This reaction includes two concessive steps: bromination of 2-arylbenzoxazoles and subsequent borylation. T...
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| Veröffentlicht in: | Tetrahedron 2011-08, Vol.67 (34), p.6191-6196 |
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| creator | Leng, Yuting Yang, Fan Zhu, Weiguo Zou, Dapeng Wu, Yangjie Cai, Ranran |
| description | An efficient and facile synthesis of arylboronic esters bearing the benzoxazole moiety has been described using a new family of palladacycle: cyclopalladated ferrocenylimines as the catalysts. This reaction includes two concessive steps: bromination of 2-arylbenzoxazoles and subsequent borylation. The bromination of
para-C–H bond was an electrophilic substitution process by using NBS as the brominating reagent, and the brominated products were determined by HMBC (
1H-detected heteronuclear multiple bond correlation) spectra. Particularly, the borylation step could be carried out successively only after removal of the solvent to afford the arylboronic esters in moderate to good yields.
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| doi_str_mv | 10.1016/j.tet.2011.06.057 |
| format | Article |
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para-C–H bond was an electrophilic substitution process by using NBS as the brominating reagent, and the brominated products were determined by HMBC (
1H-detected heteronuclear multiple bond correlation) spectra. Particularly, the borylation step could be carried out successively only after removal of the solvent to afford the arylboronic esters in moderate to good yields.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2011.06.057</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Bonding ; Borylation ; Bromination ; Catalysis ; catalysts ; Catalysts: preparations and properties ; chemical structure ; Chemistry ; Correlation ; Esters ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; HMBC spectra ; new family ; Organic chemistry ; Palladium catalysis ; Preparations and properties ; Solvents ; Spectra ; Synthesis (chemistry) ; Tetrahedrons ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Tetrahedron, 2011-08, Vol.67 (34), p.6191-6196</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c393t-4e67067636fba71265e655f3ea9f100eab492c4c218b951f410345637611e2fe3</citedby><cites>FETCH-LOGICAL-c393t-4e67067636fba71265e655f3ea9f100eab492c4c218b951f410345637611e2fe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040402011009410$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24355542$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Leng, Yuting</creatorcontrib><creatorcontrib>Yang, Fan</creatorcontrib><creatorcontrib>Zhu, Weiguo</creatorcontrib><creatorcontrib>Zou, Dapeng</creatorcontrib><creatorcontrib>Wu, Yangjie</creatorcontrib><creatorcontrib>Cai, Ranran</creatorcontrib><title>Facile synthesis of arylboronic esters by palladacycle-catalyzed bromination of 2-arylbenzoxazoles and subsequent borylation of the brominated products</title><title>Tetrahedron</title><description>An efficient and facile synthesis of arylboronic esters bearing the benzoxazole moiety has been described using a new family of palladacycle: cyclopalladated ferrocenylimines as the catalysts. This reaction includes two concessive steps: bromination of 2-arylbenzoxazoles and subsequent borylation. The bromination of
para-C–H bond was an electrophilic substitution process by using NBS as the brominating reagent, and the brominated products were determined by HMBC (
1H-detected heteronuclear multiple bond correlation) spectra. Particularly, the borylation step could be carried out successively only after removal of the solvent to afford the arylboronic esters in moderate to good yields.
[Display omitted]</description><subject>Bonding</subject><subject>Borylation</subject><subject>Bromination</subject><subject>Catalysis</subject><subject>catalysts</subject><subject>Catalysts: preparations and properties</subject><subject>chemical structure</subject><subject>Chemistry</subject><subject>Correlation</subject><subject>Esters</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>HMBC spectra</subject><subject>new family</subject><subject>Organic chemistry</subject><subject>Palladium catalysis</subject><subject>Preparations and properties</subject><subject>Solvents</subject><subject>Spectra</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><subject>Theory of reactions, general kinetics. Catalysis. 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Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leng, Yuting</creatorcontrib><creatorcontrib>Yang, Fan</creatorcontrib><creatorcontrib>Zhu, Weiguo</creatorcontrib><creatorcontrib>Zou, Dapeng</creatorcontrib><creatorcontrib>Wu, Yangjie</creatorcontrib><creatorcontrib>Cai, Ranran</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Leng, Yuting</au><au>Yang, Fan</au><au>Zhu, Weiguo</au><au>Zou, Dapeng</au><au>Wu, Yangjie</au><au>Cai, Ranran</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile synthesis of arylboronic esters by palladacycle-catalyzed bromination of 2-arylbenzoxazoles and subsequent borylation of the brominated products</atitle><jtitle>Tetrahedron</jtitle><date>2011-08-26</date><risdate>2011</risdate><volume>67</volume><issue>34</issue><spage>6191</spage><epage>6196</epage><pages>6191-6196</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>An efficient and facile synthesis of arylboronic esters bearing the benzoxazole moiety has been described using a new family of palladacycle: cyclopalladated ferrocenylimines as the catalysts. This reaction includes two concessive steps: bromination of 2-arylbenzoxazoles and subsequent borylation. The bromination of
para-C–H bond was an electrophilic substitution process by using NBS as the brominating reagent, and the brominated products were determined by HMBC (
1H-detected heteronuclear multiple bond correlation) spectra. Particularly, the borylation step could be carried out successively only after removal of the solvent to afford the arylboronic esters in moderate to good yields.
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| subjects | Bonding Borylation Bromination Catalysis catalysts Catalysts: preparations and properties chemical structure Chemistry Correlation Esters Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms HMBC spectra new family Organic chemistry Palladium catalysis Preparations and properties Solvents Spectra Synthesis (chemistry) Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Facile synthesis of arylboronic esters by palladacycle-catalyzed bromination of 2-arylbenzoxazoles and subsequent borylation of the brominated products |
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