Copper-Catalyzed Propargylation of Nitroalkanes

Copper-Catalyzed Propargylation of Nitroalkanes

Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α–functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2020-10, Vol.22 (20), p.8106-8110
Hauptverfasser: Kim, Raphael S., Dinh-Nguyen, Linh V., Shimkin, Kirk W., Watson, Donald A.
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 8110
container_issue 20
container_start_page 8106
container_title Organic letters
container_volume 22
creator Kim, Raphael S.
Dinh-Nguyen, Linh V.
Shimkin, Kirk W.
Watson, Donald A.
description Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α–functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N- heterocycles such as pyrroles and 2-pyrrolines.
doi_str_mv 10.1021/acs.orglett.0c03061
format Article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7579671</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2448406883</sourcerecordid><originalsourceid>FETCH-LOGICAL-c382t-3581f95f9091cd909f4f81bb18f33b0f7ba165bb6532f7e32f43dd2ff0e4254a3</originalsourceid><addsrcrecordid>eNpVkMtOwzAQRS0EoqXwBWy6ZJN2_EyyQUIRL6kCFrC2nMQuATcOtotUvh6jRpXY3BnNXN3RHIQuMSwwELxUTVg4v7Y6xgU0QEHgIzTFnNAsB06OD72ACToL4QMAp0l5iiaUAogS8BQtKzcM2meVisrufnQ7f_FuUH69syp2rp87M3_qonfKfqpeh3N0YpQN-mKsM_R2d_taPWSr5_vH6maVNbQgMaO8wKbkpoQSN21Sw0yB6xoXhtIaTF4rLHhdC06JyXUSRtuWGAOaEc4UnaHrfe6wrTe6bXQfvbJy8N1G-Z10qpP_N333LtfuW-Y8L0WOU8DVGODd11aHKDddaLS16Qu3DZIwVjAQRUGTle6tjXcheG0OZzDIP9QyoZYjajmipr_bgnSe</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2448406883</pqid></control><display><type>article</type><title>Copper-Catalyzed Propargylation of Nitroalkanes</title><source>American Chemical Society Journals</source><creator>Kim, Raphael S. ; Dinh-Nguyen, Linh V. ; Shimkin, Kirk W. ; Watson, Donald A.</creator><creatorcontrib>Kim, Raphael S. ; Dinh-Nguyen, Linh V. ; Shimkin, Kirk W. ; Watson, Donald A.</creatorcontrib><description>Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α–functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N- heterocycles such as pyrroles and 2-pyrrolines.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.0c03061</identifier><identifier>PMID: 33006901</identifier><language>eng</language><ispartof>Organic letters, 2020-10, Vol.22 (20), p.8106-8110</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c382t-3581f95f9091cd909f4f81bb18f33b0f7ba165bb6532f7e32f43dd2ff0e4254a3</citedby><cites>FETCH-LOGICAL-c382t-3581f95f9091cd909f4f81bb18f33b0f7ba165bb6532f7e32f43dd2ff0e4254a3</cites><orcidid>0000-0003-2259-4439 ; 0000-0003-4864-297X ; 0000-0001-8025-5166 ; 0000-0001-7739-3891</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,2765,27924,27925</link.rule.ids></links><search><creatorcontrib>Kim, Raphael S.</creatorcontrib><creatorcontrib>Dinh-Nguyen, Linh V.</creatorcontrib><creatorcontrib>Shimkin, Kirk W.</creatorcontrib><creatorcontrib>Watson, Donald A.</creatorcontrib><title>Copper-Catalyzed Propargylation of Nitroalkanes</title><title>Organic letters</title><description>Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α–functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N- heterocycles such as pyrroles and 2-pyrrolines.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpVkMtOwzAQRS0EoqXwBWy6ZJN2_EyyQUIRL6kCFrC2nMQuATcOtotUvh6jRpXY3BnNXN3RHIQuMSwwELxUTVg4v7Y6xgU0QEHgIzTFnNAsB06OD72ACToL4QMAp0l5iiaUAogS8BQtKzcM2meVisrufnQ7f_FuUH69syp2rp87M3_qonfKfqpeh3N0YpQN-mKsM_R2d_taPWSr5_vH6maVNbQgMaO8wKbkpoQSN21Sw0yB6xoXhtIaTF4rLHhdC06JyXUSRtuWGAOaEc4UnaHrfe6wrTe6bXQfvbJy8N1G-Z10qpP_N333LtfuW-Y8L0WOU8DVGODd11aHKDddaLS16Qu3DZIwVjAQRUGTle6tjXcheG0OZzDIP9QyoZYjajmipr_bgnSe</recordid><startdate>20201016</startdate><enddate>20201016</enddate><creator>Kim, Raphael S.</creator><creator>Dinh-Nguyen, Linh V.</creator><creator>Shimkin, Kirk W.</creator><creator>Watson, Donald A.</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-2259-4439</orcidid><orcidid>https://orcid.org/0000-0003-4864-297X</orcidid><orcidid>https://orcid.org/0000-0001-8025-5166</orcidid><orcidid>https://orcid.org/0000-0001-7739-3891</orcidid></search><sort><creationdate>20201016</creationdate><title>Copper-Catalyzed Propargylation of Nitroalkanes</title><author>Kim, Raphael S. ; Dinh-Nguyen, Linh V. ; Shimkin, Kirk W. ; Watson, Donald A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c382t-3581f95f9091cd909f4f81bb18f33b0f7ba165bb6532f7e32f43dd2ff0e4254a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Raphael S.</creatorcontrib><creatorcontrib>Dinh-Nguyen, Linh V.</creatorcontrib><creatorcontrib>Shimkin, Kirk W.</creatorcontrib><creatorcontrib>Watson, Donald A.</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Raphael S.</au><au>Dinh-Nguyen, Linh V.</au><au>Shimkin, Kirk W.</au><au>Watson, Donald A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Propargylation of Nitroalkanes</atitle><jtitle>Organic letters</jtitle><date>2020-10-16</date><risdate>2020</risdate><volume>22</volume><issue>20</issue><spage>8106</spage><epage>8110</epage><pages>8106-8110</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α–functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N- heterocycles such as pyrroles and 2-pyrrolines.</abstract><pmid>33006901</pmid><doi>10.1021/acs.orglett.0c03061</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-2259-4439</orcidid><orcidid>https://orcid.org/0000-0003-4864-297X</orcidid><orcidid>https://orcid.org/0000-0001-8025-5166</orcidid><orcidid>https://orcid.org/0000-0001-7739-3891</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2020-10, Vol.22 (20), p.8106-8110
issn 1523-7060
1523-7052
language eng
recordid cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7579671
source American Chemical Society Journals
title Copper-Catalyzed Propargylation of Nitroalkanes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T18%3A09%3A44IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Copper-Catalyzed%20Propargylation%20of%20Nitroalkanes&rft.jtitle=Organic%20letters&rft.au=Kim,%20Raphael%20S.&rft.date=2020-10-16&rft.volume=22&rft.issue=20&rft.spage=8106&rft.epage=8110&rft.pages=8106-8110&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.0c03061&rft_dat=%3Cproquest_pubme%3E2448406883%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2448406883&rft_id=info:pmid/33006901&rfr_iscdi=true