Cu(II)-Catalyzed Phosphonocarboxylative Cyclization Reaction of Propargylic Amines and Phosphine Oxide with CO2
Compounds bearing organophosphorus motifs and 2-oxazolidinone have found numerous applications in pharmaceutical chemistry, homogeneous catalysis, and organic materials. Here, we describe an efficient and selective protocol for straightforward access to a series of 5-((diarylphosphoryl)methyl)oxaz...
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2020-11, Vol.85 (21), p.14109-14120 |
---|---|
Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 14120 |
---|---|
container_issue | 21 |
container_start_page | 14109 |
container_title | Journal of organic chemistry |
container_volume | 85 |
creator | Huang, Wen-Bin Ren, Fang-Yu Wang, Ming-Wei Qiu, Li-Qi Chen, Kai-Hong He, Liang-Nian |
description | Compounds bearing organophosphorus motifs and 2-oxazolidinone have found numerous applications in pharmaceutical chemistry, homogeneous catalysis, and organic materials. Here, we describe an efficient and selective protocol for straightforward access to a series of 5-((diarylphosphoryl)methyl)oxazolidin-2-ones via the copper-catalyzed difunctionalization of the CC bond of propargylic amines with CO2 and phosphine oxide. Notably, copper catalysis is a sustainable and benign catalytic mode. This reaction proceeds under mild reaction conditions, which is operationally simple and scalable with a broad scope, exclusive selectivity, and good functional group compatibility. Mechanistic studies suggest a one-pot tandem cyclization/radical addition sequence, along with the phosphorylation/cyclization scheme. |
doi_str_mv | 10.1021/acs.joc.0c02172 |
format | Article |
fullrecord | <record><control><sourceid>proquest_acs_j</sourceid><recordid>TN_cdi_proquest_miscellaneous_2455835464</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2455835464</sourcerecordid><originalsourceid>FETCH-LOGICAL-a224t-c6994800a1f48d46f884c9749cd486638a6cd1bb6f72ea65dfcca523ed0f9a343</originalsourceid><addsrcrecordid>eNo1kM1Lw0AQxRdRsFbPXvdYkdT9bnIswY9CoUX0vEwnG5uSZms20aZ_vanVucx7w-Mx_Ai55WzMmeAPgGG88Thm2LuJOCMDrgWLTMLUORkwJkQkhZGX5CqEDetHaz0gPm1Hs9ldlEIDZXdwGV2ufditfeUR6pXfdyU0xZejaYdlcei1r-irA_wVPqfL2u-g_ujKAul0W1QuUKj-W3pLF_sic_S7aNY0XYhrcpFDGdzN3x6S96fHt_Qlmi-eZ-l0HoEQqonQJImKGQOeqzhTJo9jhclEJZip2BgZg8GMr1YmnwgHRmc5ImghXcbyBKSSQzI69e5q_9m60NhtEdCVJVTOt8EKpXUstTLH6P0p2hO0G9_WVf-Y5cwesdrTEe0fVvkD7mptZg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2455835464</pqid></control><display><type>article</type><title>Cu(II)-Catalyzed Phosphonocarboxylative Cyclization Reaction of Propargylic Amines and Phosphine Oxide with CO2</title><source>ACS Publications</source><creator>Huang, Wen-Bin ; Ren, Fang-Yu ; Wang, Ming-Wei ; Qiu, Li-Qi ; Chen, Kai-Hong ; He, Liang-Nian</creator><creatorcontrib>Huang, Wen-Bin ; Ren, Fang-Yu ; Wang, Ming-Wei ; Qiu, Li-Qi ; Chen, Kai-Hong ; He, Liang-Nian</creatorcontrib><description>Compounds bearing organophosphorus motifs and 2-oxazolidinone have found numerous applications in pharmaceutical chemistry, homogeneous catalysis, and organic materials. Here, we describe an efficient and selective protocol for straightforward access to a series of 5-((diarylphosphoryl)methyl)oxazolidin-2-ones via the copper-catalyzed difunctionalization of the CC bond of propargylic amines with CO2 and phosphine oxide. Notably, copper catalysis is a sustainable and benign catalytic mode. This reaction proceeds under mild reaction conditions, which is operationally simple and scalable with a broad scope, exclusive selectivity, and good functional group compatibility. Mechanistic studies suggest a one-pot tandem cyclization/radical addition sequence, along with the phosphorylation/cyclization scheme.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.0c02172</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2020-11, Vol.85 (21), p.14109-14120</ispartof><rights>2020 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-6067-5937</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.0c02172$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.0c02172$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27055,27903,27904,56716,56766</link.rule.ids></links><search><creatorcontrib>Huang, Wen-Bin</creatorcontrib><creatorcontrib>Ren, Fang-Yu</creatorcontrib><creatorcontrib>Wang, Ming-Wei</creatorcontrib><creatorcontrib>Qiu, Li-Qi</creatorcontrib><creatorcontrib>Chen, Kai-Hong</creatorcontrib><creatorcontrib>He, Liang-Nian</creatorcontrib><title>Cu(II)-Catalyzed Phosphonocarboxylative Cyclization Reaction of Propargylic Amines and Phosphine Oxide with CO2</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Compounds bearing organophosphorus motifs and 2-oxazolidinone have found numerous applications in pharmaceutical chemistry, homogeneous catalysis, and organic materials. Here, we describe an efficient and selective protocol for straightforward access to a series of 5-((diarylphosphoryl)methyl)oxazolidin-2-ones via the copper-catalyzed difunctionalization of the CC bond of propargylic amines with CO2 and phosphine oxide. Notably, copper catalysis is a sustainable and benign catalytic mode. This reaction proceeds under mild reaction conditions, which is operationally simple and scalable with a broad scope, exclusive selectivity, and good functional group compatibility. Mechanistic studies suggest a one-pot tandem cyclization/radical addition sequence, along with the phosphorylation/cyclization scheme.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNo1kM1Lw0AQxRdRsFbPXvdYkdT9bnIswY9CoUX0vEwnG5uSZms20aZ_vanVucx7w-Mx_Ai55WzMmeAPgGG88Thm2LuJOCMDrgWLTMLUORkwJkQkhZGX5CqEDetHaz0gPm1Hs9ldlEIDZXdwGV2ufditfeUR6pXfdyU0xZejaYdlcei1r-irA_wVPqfL2u-g_ujKAul0W1QuUKj-W3pLF_sic_S7aNY0XYhrcpFDGdzN3x6S96fHt_Qlmi-eZ-l0HoEQqonQJImKGQOeqzhTJo9jhclEJZip2BgZg8GMr1YmnwgHRmc5ImghXcbyBKSSQzI69e5q_9m60NhtEdCVJVTOt8EKpXUstTLH6P0p2hO0G9_WVf-Y5cwesdrTEe0fVvkD7mptZg</recordid><startdate>20201106</startdate><enddate>20201106</enddate><creator>Huang, Wen-Bin</creator><creator>Ren, Fang-Yu</creator><creator>Wang, Ming-Wei</creator><creator>Qiu, Li-Qi</creator><creator>Chen, Kai-Hong</creator><creator>He, Liang-Nian</creator><general>American Chemical Society</general><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6067-5937</orcidid></search><sort><creationdate>20201106</creationdate><title>Cu(II)-Catalyzed Phosphonocarboxylative Cyclization Reaction of Propargylic Amines and Phosphine Oxide with CO2</title><author>Huang, Wen-Bin ; Ren, Fang-Yu ; Wang, Ming-Wei ; Qiu, Li-Qi ; Chen, Kai-Hong ; He, Liang-Nian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a224t-c6994800a1f48d46f884c9749cd486638a6cd1bb6f72ea65dfcca523ed0f9a343</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Wen-Bin</creatorcontrib><creatorcontrib>Ren, Fang-Yu</creatorcontrib><creatorcontrib>Wang, Ming-Wei</creatorcontrib><creatorcontrib>Qiu, Li-Qi</creatorcontrib><creatorcontrib>Chen, Kai-Hong</creatorcontrib><creatorcontrib>He, Liang-Nian</creatorcontrib><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Wen-Bin</au><au>Ren, Fang-Yu</au><au>Wang, Ming-Wei</au><au>Qiu, Li-Qi</au><au>Chen, Kai-Hong</au><au>He, Liang-Nian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cu(II)-Catalyzed Phosphonocarboxylative Cyclization Reaction of Propargylic Amines and Phosphine Oxide with CO2</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2020-11-06</date><risdate>2020</risdate><volume>85</volume><issue>21</issue><spage>14109</spage><epage>14120</epage><pages>14109-14120</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Compounds bearing organophosphorus motifs and 2-oxazolidinone have found numerous applications in pharmaceutical chemistry, homogeneous catalysis, and organic materials. Here, we describe an efficient and selective protocol for straightforward access to a series of 5-((diarylphosphoryl)methyl)oxazolidin-2-ones via the copper-catalyzed difunctionalization of the CC bond of propargylic amines with CO2 and phosphine oxide. Notably, copper catalysis is a sustainable and benign catalytic mode. This reaction proceeds under mild reaction conditions, which is operationally simple and scalable with a broad scope, exclusive selectivity, and good functional group compatibility. Mechanistic studies suggest a one-pot tandem cyclization/radical addition sequence, along with the phosphorylation/cyclization scheme.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.joc.0c02172</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-6067-5937</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0022-3263 |
ispartof | Journal of organic chemistry, 2020-11, Vol.85 (21), p.14109-14120 |
issn | 0022-3263 1520-6904 |
language | eng |
recordid | cdi_proquest_miscellaneous_2455835464 |
source | ACS Publications |
title | Cu(II)-Catalyzed Phosphonocarboxylative Cyclization Reaction of Propargylic Amines and Phosphine Oxide with CO2 |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-25T16%3A35%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_acs_j&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Cu(II)-Catalyzed%20Phosphonocarboxylative%20Cyclization%20Reaction%20of%20Propargylic%20Amines%20and%20Phosphine%20Oxide%20with%20CO2&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Huang,%20Wen-Bin&rft.date=2020-11-06&rft.volume=85&rft.issue=21&rft.spage=14109&rft.epage=14120&rft.pages=14109-14120&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.0c02172&rft_dat=%3Cproquest_acs_j%3E2455835464%3C/proquest_acs_j%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2455835464&rft_id=info:pmid/&rfr_iscdi=true |