Enantioselective cyanation of propargylic C-H bonds via cooperative photoredox and copper catalysis

Herein, we report an enantioselective cyanation of propargylic C-H bonds by combining photoredox catalysis with a copper-catalyzed radical relay in which the propargylic radical was generated by an intramolecular 1,5-HAT process. This reaction provides easy access to optically pure propargyl nitrile...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2023-04, Vol.59 (31), p.4656-4659
Hauptverfasser:	Deng, Yunshun, Lu, Ronghua, Chen, Pinhong, Liu, Guosheng
Format:	Artikel
Sprache:	eng
Schlagworte:	Copper Enantiomers Photoredox catalysis
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	4659
container_issue	31
container_start_page	4656
container_title	Chemical communications (Cambridge, England)
container_volume	59
creator	Deng, Yunshun Lu, Ronghua Chen, Pinhong Liu, Guosheng
description	Herein, we report an enantioselective cyanation of propargylic C-H bonds by combining photoredox catalysis with a copper-catalyzed radical relay in which the propargylic radical was generated by an intramolecular 1,5-HAT process. This reaction provides easy access to optically pure propargyl nitrile compounds under mild conditions.
doi_str_mv	10.1039/d3cc00410d
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2792502434</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2800137724</sourcerecordid><originalsourceid>FETCH-LOGICAL-c351t-25bb13c1f3eb721a0c99d4158e71894ab69101ece103a206e8b8e1591f3afc6e3</originalsourceid><addsrcrecordid>eNpdkE1Lw0AQhhdRbK1e_AGy4EWE6H7lY4-SVisUvCh4C5vNRFPS3bibFPvv3X7owbnMMPPM8M6L0CUld5RweV9xrQkRlFRHaEx5IqJYZO_H2zqWUcpFPEJn3i9JCBpnp2jEE5llnIkx0jOjTN9YDy3ovlkD1htlVOgYbGvcOdsp97FpG43zaI5LayqP143C2toOnNqtdJ-2tw4q-42VqcKoCyOsVa_ajW_8OTqpVevh4pAn6O1x9prPo8XL03P-sIg0j2kfsbgsKde05lCmjCqipaxEEAwpzaRQZSIpoaAhPK0YSSArM6CxDAuq1gnwCbrZ3w2qvwbwfbFqvIa2VQbs4AuWShYTJrgI6PU_dGkHZ4K6gmXBJZ6mbEvd7intrPcO6qJzzUq5TUFJsbW-mPI831k_DfDV4eRQrqD6Q3-95j-t4n74</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2800137724</pqid></control><display><type>article</type><title>Enantioselective cyanation of propargylic C-H bonds via cooperative photoredox and copper catalysis</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Deng, Yunshun ; Lu, Ronghua ; Chen, Pinhong ; Liu, Guosheng</creator><creatorcontrib>Deng, Yunshun ; Lu, Ronghua ; Chen, Pinhong ; Liu, Guosheng</creatorcontrib><description>Herein, we report an enantioselective cyanation of propargylic C-H bonds by combining photoredox catalysis with a copper-catalyzed radical relay in which the propargylic radical was generated by an intramolecular 1,5-HAT process. This reaction provides easy access to optically pure propargyl nitrile compounds under mild conditions.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d3cc00410d</identifier><identifier>PMID: 36988324</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Copper ; Enantiomers ; Photoredox catalysis</subject><ispartof>Chemical communications (Cambridge, England), 2023-04, Vol.59 (31), p.4656-4659</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c351t-25bb13c1f3eb721a0c99d4158e71894ab69101ece103a206e8b8e1591f3afc6e3</citedby><cites>FETCH-LOGICAL-c351t-25bb13c1f3eb721a0c99d4158e71894ab69101ece103a206e8b8e1591f3afc6e3</cites><orcidid>0000-0003-0572-9370 ; 0000-0001-5048-1445</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36988324$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Deng, Yunshun</creatorcontrib><creatorcontrib>Lu, Ronghua</creatorcontrib><creatorcontrib>Chen, Pinhong</creatorcontrib><creatorcontrib>Liu, Guosheng</creatorcontrib><title>Enantioselective cyanation of propargylic C-H bonds via cooperative photoredox and copper catalysis</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Herein, we report an enantioselective cyanation of propargylic C-H bonds by combining photoredox catalysis with a copper-catalyzed radical relay in which the propargylic radical was generated by an intramolecular 1,5-HAT process. This reaction provides easy access to optically pure propargyl nitrile compounds under mild conditions.</description><subject>Copper</subject><subject>Enantiomers</subject><subject>Photoredox catalysis</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkE1Lw0AQhhdRbK1e_AGy4EWE6H7lY4-SVisUvCh4C5vNRFPS3bibFPvv3X7owbnMMPPM8M6L0CUld5RweV9xrQkRlFRHaEx5IqJYZO_H2zqWUcpFPEJn3i9JCBpnp2jEE5llnIkx0jOjTN9YDy3ovlkD1htlVOgYbGvcOdsp97FpG43zaI5LayqP143C2toOnNqtdJ-2tw4q-42VqcKoCyOsVa_ajW_8OTqpVevh4pAn6O1x9prPo8XL03P-sIg0j2kfsbgsKde05lCmjCqipaxEEAwpzaRQZSIpoaAhPK0YSSArM6CxDAuq1gnwCbrZ3w2qvwbwfbFqvIa2VQbs4AuWShYTJrgI6PU_dGkHZ4K6gmXBJZ6mbEvd7intrPcO6qJzzUq5TUFJsbW-mPI831k_DfDV4eRQrqD6Q3-95j-t4n74</recordid><startdate>20230413</startdate><enddate>20230413</enddate><creator>Deng, Yunshun</creator><creator>Lu, Ronghua</creator><creator>Chen, Pinhong</creator><creator>Liu, Guosheng</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0572-9370</orcidid><orcidid>https://orcid.org/0000-0001-5048-1445</orcidid></search><sort><creationdate>20230413</creationdate><title>Enantioselective cyanation of propargylic C-H bonds via cooperative photoredox and copper catalysis</title><author>Deng, Yunshun ; Lu, Ronghua ; Chen, Pinhong ; Liu, Guosheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c351t-25bb13c1f3eb721a0c99d4158e71894ab69101ece103a206e8b8e1591f3afc6e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Copper</topic><topic>Enantiomers</topic><topic>Photoredox catalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Deng, Yunshun</creatorcontrib><creatorcontrib>Lu, Ronghua</creatorcontrib><creatorcontrib>Chen, Pinhong</creatorcontrib><creatorcontrib>Liu, Guosheng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</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><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Deng, Yunshun</au><au>Lu, Ronghua</au><au>Chen, Pinhong</au><au>Liu, Guosheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective cyanation of propargylic C-H bonds via cooperative photoredox and copper catalysis</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2023-04-13</date><risdate>2023</risdate><volume>59</volume><issue>31</issue><spage>4656</spage><epage>4659</epage><pages>4656-4659</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Herein, we report an enantioselective cyanation of propargylic C-H bonds by combining photoredox catalysis with a copper-catalyzed radical relay in which the propargylic radical was generated by an intramolecular 1,5-HAT process. This reaction provides easy access to optically pure propargyl nitrile compounds under mild conditions.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36988324</pmid><doi>10.1039/d3cc00410d</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-0572-9370</orcidid><orcidid>https://orcid.org/0000-0001-5048-1445</orcidid><oa>free_for_read</oa></addata></record>
fulltext	fulltext
identifier	ISSN: 1359-7345
ispartof	Chemical communications (Cambridge, England), 2023-04, Vol.59 (31), p.4656-4659
issn	1359-7345 1364-548X
language	eng
recordid	cdi_proquest_miscellaneous_2792502434
source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Copper Enantiomers Photoredox catalysis
title	Enantioselective cyanation of propargylic C-H bonds via cooperative photoredox and copper catalysis
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-26T20%3A39%3A05IST&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=Enantioselective%20cyanation%20of%20propargylic%20C-H%20bonds%20via%20cooperative%20photoredox%20and%20copper%20catalysis&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Deng,%20Yunshun&rft.date=2023-04-13&rft.volume=59&rft.issue=31&rft.spage=4656&rft.epage=4659&rft.pages=4656-4659&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d3cc00410d&rft_dat=%3Cproquest_cross%3E2800137724%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=2800137724&rft_id=info:pmid/36988324&rfr_iscdi=true