Metal‐Free Decarboxylation of Alkynoic Acids for the Synthesis of Terminal Alkynes
Terminal alkynes were readily obtained via the reaction of alkynoic acids with N,N,N’,N’‐teramethylethylenediamine (TMEDA) in DMSO at 65 °C for 12 h. This method gave good yields and showed high functional group tolerance. In addition, deuterated terminal alkynes were formed in good yields when alky...
Gespeichert in:
Veröffentlicht in: | Asian journal of organic chemistry 2020-11, Vol.9 (11), p.1774-1777 |
---|---|
Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 1777 |
---|---|
container_issue | 11 |
container_start_page | 1774 |
container_title | Asian journal of organic chemistry |
container_volume | 9 |
creator | Seo, Eunkyeong Oh, Jonghoon Lee, Sunwoo |
description | Terminal alkynes were readily obtained via the reaction of alkynoic acids with N,N,N’,N’‐teramethylethylenediamine (TMEDA) in DMSO at 65 °C for 12 h. This method gave good yields and showed high functional group tolerance. In addition, deuterated terminal alkynes were formed in good yields when alkynoic acids were treated with D2O prior to the reaction with TMEDA.
In the presence of TMEDA, alkynoic acid derivatives afforded the corresponding terminal alkynes in good yields. |
doi_str_mv | 10.1002/ajoc.202000363 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2460968504</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2460968504</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3173-e0bdf3a883cd1715d3c8650ff696fae539a8f8307a929ed0a079128fc158f6503</originalsourceid><addsrcrecordid>eNqFkL1OwzAUhS0EElXpymyJOeU6rhN7jArlR0UMlNlyHVu4pHGxU0E2HoFn5ElIFFRGpnOH77s6OgidE5gSgPRSbbyeppACAM3oERqlRNCEccKODzfkp2gS46ZjIM8FScUIrR5Mo6rvz69FMAZfGa3C2n-0lWqcr7G3uKhe29o7jQvtyoitD7h5MfiprbuILvbMyoStq1U1wCaeoROrqmgmvzlGz4vr1fw2WT7e3M2LZaIpyWliYF1aqjinuiQ5YSXVPGNgbSYyqwyjQnHLKeRKpMKUoKAvza0mjNsOpGN0MfzdBf-2N7GRG78PXZEo01kGIuMMZh01HSgdfIzBWLkLbqtCKwnIfjzZjycP43WCGIR3V5n2H1oW94_zP_cHPXtzQA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2460968504</pqid></control><display><type>article</type><title>Metal‐Free Decarboxylation of Alkynoic Acids for the Synthesis of Terminal Alkynes</title><source>Wiley-Blackwell Full Collection</source><creator>Seo, Eunkyeong ; Oh, Jonghoon ; Lee, Sunwoo</creator><creatorcontrib>Seo, Eunkyeong ; Oh, Jonghoon ; Lee, Sunwoo</creatorcontrib><description>Terminal alkynes were readily obtained via the reaction of alkynoic acids with N,N,N’,N’‐teramethylethylenediamine (TMEDA) in DMSO at 65 °C for 12 h. This method gave good yields and showed high functional group tolerance. In addition, deuterated terminal alkynes were formed in good yields when alkynoic acids were treated with D2O prior to the reaction with TMEDA.
In the presence of TMEDA, alkynoic acid derivatives afforded the corresponding terminal alkynes in good yields.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202000363</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; alkynoic aicd ; Decarboxylation ; Deuteration ; Functional groups ; metal-free conditions ; Organic chemistry ; terminal alkyne</subject><ispartof>Asian journal of organic chemistry, 2020-11, Vol.9 (11), p.1774-1777</ispartof><rights>2020 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3173-e0bdf3a883cd1715d3c8650ff696fae539a8f8307a929ed0a079128fc158f6503</citedby><cites>FETCH-LOGICAL-c3173-e0bdf3a883cd1715d3c8650ff696fae539a8f8307a929ed0a079128fc158f6503</cites><orcidid>0000-0001-5079-3860</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fajoc.202000363$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202000363$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Seo, Eunkyeong</creatorcontrib><creatorcontrib>Oh, Jonghoon</creatorcontrib><creatorcontrib>Lee, Sunwoo</creatorcontrib><title>Metal‐Free Decarboxylation of Alkynoic Acids for the Synthesis of Terminal Alkynes</title><title>Asian journal of organic chemistry</title><description>Terminal alkynes were readily obtained via the reaction of alkynoic acids with N,N,N’,N’‐teramethylethylenediamine (TMEDA) in DMSO at 65 °C for 12 h. This method gave good yields and showed high functional group tolerance. In addition, deuterated terminal alkynes were formed in good yields when alkynoic acids were treated with D2O prior to the reaction with TMEDA.
In the presence of TMEDA, alkynoic acid derivatives afforded the corresponding terminal alkynes in good yields.</description><subject>Alkynes</subject><subject>alkynoic aicd</subject><subject>Decarboxylation</subject><subject>Deuteration</subject><subject>Functional groups</subject><subject>metal-free conditions</subject><subject>Organic chemistry</subject><subject>terminal alkyne</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAUhS0EElXpymyJOeU6rhN7jArlR0UMlNlyHVu4pHGxU0E2HoFn5ElIFFRGpnOH77s6OgidE5gSgPRSbbyeppACAM3oERqlRNCEccKODzfkp2gS46ZjIM8FScUIrR5Mo6rvz69FMAZfGa3C2n-0lWqcr7G3uKhe29o7jQvtyoitD7h5MfiprbuILvbMyoStq1U1wCaeoROrqmgmvzlGz4vr1fw2WT7e3M2LZaIpyWliYF1aqjinuiQ5YSXVPGNgbSYyqwyjQnHLKeRKpMKUoKAvza0mjNsOpGN0MfzdBf-2N7GRG78PXZEo01kGIuMMZh01HSgdfIzBWLkLbqtCKwnIfjzZjycP43WCGIR3V5n2H1oW94_zP_cHPXtzQA</recordid><startdate>202011</startdate><enddate>202011</enddate><creator>Seo, Eunkyeong</creator><creator>Oh, Jonghoon</creator><creator>Lee, Sunwoo</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-5079-3860</orcidid></search><sort><creationdate>202011</creationdate><title>Metal‐Free Decarboxylation of Alkynoic Acids for the Synthesis of Terminal Alkynes</title><author>Seo, Eunkyeong ; Oh, Jonghoon ; Lee, Sunwoo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3173-e0bdf3a883cd1715d3c8650ff696fae539a8f8307a929ed0a079128fc158f6503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkynes</topic><topic>alkynoic aicd</topic><topic>Decarboxylation</topic><topic>Deuteration</topic><topic>Functional groups</topic><topic>metal-free conditions</topic><topic>Organic chemistry</topic><topic>terminal alkyne</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Seo, Eunkyeong</creatorcontrib><creatorcontrib>Oh, Jonghoon</creatorcontrib><creatorcontrib>Lee, Sunwoo</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Seo, Eunkyeong</au><au>Oh, Jonghoon</au><au>Lee, Sunwoo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal‐Free Decarboxylation of Alkynoic Acids for the Synthesis of Terminal Alkynes</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2020-11</date><risdate>2020</risdate><volume>9</volume><issue>11</issue><spage>1774</spage><epage>1777</epage><pages>1774-1777</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>Terminal alkynes were readily obtained via the reaction of alkynoic acids with N,N,N’,N’‐teramethylethylenediamine (TMEDA) in DMSO at 65 °C for 12 h. This method gave good yields and showed high functional group tolerance. In addition, deuterated terminal alkynes were formed in good yields when alkynoic acids were treated with D2O prior to the reaction with TMEDA.
In the presence of TMEDA, alkynoic acid derivatives afforded the corresponding terminal alkynes in good yields.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202000363</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-5079-3860</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 2193-5807 |
ispartof | Asian journal of organic chemistry, 2020-11, Vol.9 (11), p.1774-1777 |
issn | 2193-5807 2193-5815 |
language | eng |
recordid | cdi_proquest_journals_2460968504 |
source | Wiley-Blackwell Full Collection |
subjects | Alkynes alkynoic aicd Decarboxylation Deuteration Functional groups metal-free conditions Organic chemistry terminal alkyne |
title | Metal‐Free Decarboxylation of Alkynoic Acids for the Synthesis of Terminal Alkynes |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-29T07%3A31%3A45IST&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=Metal%E2%80%90Free%20Decarboxylation%20of%20Alkynoic%20Acids%20for%20the%20Synthesis%20of%20Terminal%20Alkynes&rft.jtitle=Asian%20journal%20of%20organic%20chemistry&rft.au=Seo,%20Eunkyeong&rft.date=2020-11&rft.volume=9&rft.issue=11&rft.spage=1774&rft.epage=1777&rft.pages=1774-1777&rft.issn=2193-5807&rft.eissn=2193-5815&rft_id=info:doi/10.1002/ajoc.202000363&rft_dat=%3Cproquest_cross%3E2460968504%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=2460968504&rft_id=info:pmid/&rfr_iscdi=true |