Competition Studies in Alkyne Electrophilic Cyclization Reactions
The relative reactivity of various functional groups toward alkyne electrophilic cyclization reactions has been studied. The required diarylalkynes have been prepared by consecutive Sonogashira reactions of appropriately substituted aryl halides and competitive cyclizations have been performed using...
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| Veröffentlicht in: | Journal of organic chemistry 2009-02, Vol.74 (3), p.1141-1147 |
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| container_end_page | 1147 |
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| container_issue | 3 |
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| container_title | Journal of organic chemistry |
| container_volume | 74 |
| creator | Mehta, Saurabh Waldo, Jesse P Larock, Richard C |
| description | The relative reactivity of various functional groups toward alkyne electrophilic cyclization reactions has been studied. The required diarylalkynes have been prepared by consecutive Sonogashira reactions of appropriately substituted aryl halides and competitive cyclizations have been performed using I2, ICl, NBS and PhSeCl as electrophiles. The results indicate that the nucleophilicity of the competing functional groups, polarization of the alkyne triple bond, and the cationic nature of the intermediate are the most important factors in determining the outcome of these reactions. |
| doi_str_mv | 10.1021/jo802196r |
| format | Article |
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The required diarylalkynes have been prepared by consecutive Sonogashira reactions of appropriately substituted aryl halides and competitive cyclizations have been performed using I2, ICl, NBS and PhSeCl as electrophiles. The results indicate that the nucleophilicity of the competing functional groups, polarization of the alkyne triple bond, and the cationic nature of the intermediate are the most important factors in determining the outcome of these reactions.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo802196r</identifier><identifier>PMID: 19105638</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkynes - chemical synthesis ; Alkynes - chemistry ; Benzene Derivatives - chemistry ; Chemical reactivity ; Chemistry ; Cyclization ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Heterocyclic Compounds, 2-Ring - chemical synthesis ; Heterocyclic Compounds, 2-Ring - chemistry ; Imines - chemical synthesis ; Imines - chemistry ; Organic chemistry ; Preparations and properties ; Reactivity and mechanisms</subject><ispartof>Journal of organic chemistry, 2009-02, Vol.74 (3), p.1141-1147</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a499t-a797f41fdeea42d3216394e37a578e2513e906d082e337ef8e901a975eba71573</citedby><cites>FETCH-LOGICAL-a499t-a797f41fdeea42d3216394e37a578e2513e906d082e337ef8e901a975eba71573</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/jo802196r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo802196r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,777,781,882,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21078989$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19105638$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mehta, Saurabh</creatorcontrib><creatorcontrib>Waldo, Jesse P</creatorcontrib><creatorcontrib>Larock, Richard C</creatorcontrib><title>Competition Studies in Alkyne Electrophilic Cyclization Reactions</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The relative reactivity of various functional groups toward alkyne electrophilic cyclization reactions has been studied. The required diarylalkynes have been prepared by consecutive Sonogashira reactions of appropriately substituted aryl halides and competitive cyclizations have been performed using I2, ICl, NBS and PhSeCl as electrophiles. The results indicate that the nucleophilicity of the competing functional groups, polarization of the alkyne triple bond, and the cationic nature of the intermediate are the most important factors in determining the outcome of these reactions.</description><subject>Alkynes - chemical synthesis</subject><subject>Alkynes - chemistry</subject><subject>Benzene Derivatives - chemistry</subject><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic Compounds, 2-Ring - chemical synthesis</subject><subject>Heterocyclic Compounds, 2-Ring - chemistry</subject><subject>Imines - chemical synthesis</subject><subject>Imines - chemistry</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkFtLHEEQhRtJ0NX44B8I8xIhD2P6Mn17CSyLMQEhkMtzU_bUxNbe6bV7Rlh_vbO6rAqpl6qiPs4pDiEnjJ4xytmXm2SmZlXeIzMmOa2Vpc07MqOU81pwJQ7IYSk3dCop5T45YJZRqYSZkfkiLVc4hCGkvvo9jG3AUoW-msfbdY_VeUQ_5LS6DjH4arH2MTzAE_sLwW-G8oG87yAWPN72I_L32_mfxff68ufFj8X8sobG2qEGbXXXsK5FhIa3gjMlbINCg9QGuWQCLVUtNRyF0NiZaWVgtcQr0ExqcUS-Puuuxqslth77IUN0qxyWkNcuQXBvL324dv_SveNKcWE3AqdbgZzuRiyDW4biMUboMY3FKWWUEU9On59Bn1MpGbudCaNuE7jbBT6xH19_9UJuE56AT1sAiofYZeh9KDuOM6qNNfaFA18m_TH3U5j_MXwEVSiVLQ</recordid><startdate>20090206</startdate><enddate>20090206</enddate><creator>Mehta, Saurabh</creator><creator>Waldo, Jesse P</creator><creator>Larock, Richard C</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20090206</creationdate><title>Competition Studies in Alkyne Electrophilic Cyclization Reactions</title><author>Mehta, Saurabh ; Waldo, Jesse P ; Larock, Richard C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a499t-a797f41fdeea42d3216394e37a578e2513e906d082e337ef8e901a975eba71573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alkynes - chemical synthesis</topic><topic>Alkynes - chemistry</topic><topic>Benzene Derivatives - chemistry</topic><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Cyclization</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic Compounds, 2-Ring - chemical synthesis</topic><topic>Heterocyclic Compounds, 2-Ring - chemistry</topic><topic>Imines - chemical synthesis</topic><topic>Imines - chemistry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mehta, Saurabh</creatorcontrib><creatorcontrib>Waldo, Jesse P</creatorcontrib><creatorcontrib>Larock, Richard C</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mehta, Saurabh</au><au>Waldo, Jesse P</au><au>Larock, Richard C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Competition Studies in Alkyne Electrophilic Cyclization Reactions</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-02-06</date><risdate>2009</risdate><volume>74</volume><issue>3</issue><spage>1141</spage><epage>1147</epage><pages>1141-1147</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The relative reactivity of various functional groups toward alkyne electrophilic cyclization reactions has been studied. The required diarylalkynes have been prepared by consecutive Sonogashira reactions of appropriately substituted aryl halides and competitive cyclizations have been performed using I2, ICl, NBS and PhSeCl as electrophiles. 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| ispartof | Journal of organic chemistry, 2009-02, Vol.74 (3), p.1141-1147 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alkynes - chemical synthesis Alkynes - chemistry Benzene Derivatives - chemistry Chemical reactivity Chemistry Cyclization Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Imines - chemical synthesis Imines - chemistry Organic chemistry Preparations and properties Reactivity and mechanisms |
| title | Competition Studies in Alkyne Electrophilic Cyclization Reactions |
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