Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts
A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group...
Gespeichert in:
| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2018, Vol.54 (17), p.2130-2133 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2133 |
|---|---|
| container_issue | 17 |
| container_start_page | 2130 |
| container_title | Chemical communications (Cambridge, England) |
| container_volume | 54 |
| creator | Liu, Chengwei Szostak, Michal |
| description | A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest. |
| doi_str_mv | 10.1039/c8cc00271a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1999677057</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1999677057</sourcerecordid><originalsourceid>FETCH-LOGICAL-c381t-533fa6c238558d007b9769b87ad21561f3e0ae361cd8af852d601bdf3f6675463</originalsourceid><addsrcrecordid>eNpdkUtLw0AUhQdRbK1u_AEScCNCdB6Z17LEJxTcKLgLk8nETk0ydWYi5N-b2taFd3Mvh-8eLvcAcI7gDYJE3mqhNYSYI3UApoiwLKWZeD_czFSmnGR0Ak5CWMGxEBXHYIJlhqQgeArsndHKl64bGhXtt0ni0joTl8bb2upRcl1SDkln9adpklFQzRBsSPpgu49EWZ8mqquS1tkQe2_SEFXZmD2_9ma3EsMpOKpVE8zZrs_A28P9a_6ULl4en_P5ItVEoJhSQmrFNCaCUlFByEvJmSwFVxVGlKGaGKgMYUhXQtWC4opBVFY1qRnjNGNkBq62vmvvvnoTYtHaoE3TqM64PhRISsk4h5SP6OU_dOV6343XFRgiKLAkDI7U9ZbS3oXgTV2svW2VHwoEi00ARS7y_DeA-Qhf7Cz7sjXVH7r_OPkBj7uBWQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2010829360</pqid></control><display><type>article</type><title>Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts</title><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Liu, Chengwei ; Szostak, Michal</creator><creatorcontrib>Liu, Chengwei ; Szostak, Michal</creatorcontrib><description>A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c8cc00271a</identifier><identifier>PMID: 29419832</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Carboxylic acids ; Catalysis ; Coupling ; Cross coupling ; Cyanides ; Esters ; Functional groups ; Halides ; Ketones ; Moisture ; Nickel ; Thioesters</subject><ispartof>Chemical communications (Cambridge, England), 2018, Vol.54 (17), p.2130-2133</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-533fa6c238558d007b9769b87ad21561f3e0ae361cd8af852d601bdf3f6675463</citedby><cites>FETCH-LOGICAL-c381t-533fa6c238558d007b9769b87ad21561f3e0ae361cd8af852d601bdf3f6675463</cites><orcidid>0000-0002-9650-9690 ; 0000-0003-1297-7188</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29419832$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Chengwei</creatorcontrib><creatorcontrib>Szostak, Michal</creatorcontrib><title>Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.</description><subject>Aromatic compounds</subject><subject>Carboxylic acids</subject><subject>Catalysis</subject><subject>Coupling</subject><subject>Cross coupling</subject><subject>Cyanides</subject><subject>Esters</subject><subject>Functional groups</subject><subject>Halides</subject><subject>Ketones</subject><subject>Moisture</subject><subject>Nickel</subject><subject>Thioesters</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkUtLw0AUhQdRbK1u_AEScCNCdB6Z17LEJxTcKLgLk8nETk0ydWYi5N-b2taFd3Mvh-8eLvcAcI7gDYJE3mqhNYSYI3UApoiwLKWZeD_czFSmnGR0Ak5CWMGxEBXHYIJlhqQgeArsndHKl64bGhXtt0ni0joTl8bb2upRcl1SDkln9adpklFQzRBsSPpgu49EWZ8mqquS1tkQe2_SEFXZmD2_9ma3EsMpOKpVE8zZrs_A28P9a_6ULl4en_P5ItVEoJhSQmrFNCaCUlFByEvJmSwFVxVGlKGaGKgMYUhXQtWC4opBVFY1qRnjNGNkBq62vmvvvnoTYtHaoE3TqM64PhRISsk4h5SP6OU_dOV6343XFRgiKLAkDI7U9ZbS3oXgTV2svW2VHwoEi00ARS7y_DeA-Qhf7Cz7sjXVH7r_OPkBj7uBWQ</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Liu, Chengwei</creator><creator>Szostak, Michal</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/0000-0002-9650-9690</orcidid><orcidid>https://orcid.org/0000-0003-1297-7188</orcidid></search><sort><creationdate>2018</creationdate><title>Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts</title><author>Liu, Chengwei ; Szostak, Michal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-533fa6c238558d007b9769b87ad21561f3e0ae361cd8af852d601bdf3f6675463</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aromatic compounds</topic><topic>Carboxylic acids</topic><topic>Catalysis</topic><topic>Coupling</topic><topic>Cross coupling</topic><topic>Cyanides</topic><topic>Esters</topic><topic>Functional groups</topic><topic>Halides</topic><topic>Ketones</topic><topic>Moisture</topic><topic>Nickel</topic><topic>Thioesters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Chengwei</creatorcontrib><creatorcontrib>Szostak, Michal</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>Liu, Chengwei</au><au>Szostak, Michal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2018</date><risdate>2018</risdate><volume>54</volume><issue>17</issue><spage>2130</spage><epage>2133</epage><pages>2130-2133</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>29419832</pmid><doi>10.1039/c8cc00271a</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-9650-9690</orcidid><orcidid>https://orcid.org/0000-0003-1297-7188</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2018, Vol.54 (17), p.2130-2133 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1999677057 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Aromatic compounds Carboxylic acids Catalysis Coupling Cross coupling Cyanides Esters Functional groups Halides Ketones Moisture Nickel Thioesters |
| title | Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T05%3A01%3A11IST&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=Decarbonylative%20thioetherification%20by%20nickel%20catalysis%20using%20air-%20and%20moisture-stable%20nickel%20precatalysts&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Liu,%20Chengwei&rft.date=2018&rft.volume=54&rft.issue=17&rft.spage=2130&rft.epage=2133&rft.pages=2130-2133&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/c8cc00271a&rft_dat=%3Cproquest_cross%3E1999677057%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=2010829360&rft_id=info:pmid/29419832&rfr_iscdi=true |