A Facile synthesis of Biaryl ketones in recyclable system: Triazenes as new coupling partners in the carbonylative Suzuki and Hiyama cross‐coupling reactions using NFSac as CO source
Palladium‐catalyzed carbonylation reactions aid as potent tools for the insertion of carbonyl unit(s) in a wide array of molecules possessing vast number of applications in multiple domains. An efficient and facile protocol has been reported for the carbonylative Suzuki (CO−S) and carbonylative Hiya...
Gespeichert in:
Veröffentlicht in: | ChemistrySelect (Weinheim) 2023-06, Vol.8 (23), p.n/a |
---|---|
Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | n/a |
---|---|
container_issue | 23 |
container_start_page | |
container_title | ChemistrySelect (Weinheim) |
container_volume | 8 |
creator | Anchi, Athmanand Kalkhambkar, Rajesh G. Kumar P, Pavan Naik, Ravi S Refat, Moamen S. Adam, Abdel Majid A. Alsuhaibani, Amnah Mohammed Bakare, Safyah B. |
description | Palladium‐catalyzed carbonylation reactions aid as potent tools for the insertion of carbonyl unit(s) in a wide array of molecules possessing vast number of applications in multiple domains. An efficient and facile protocol has been reported for the carbonylative Suzuki (CO−S) and carbonylative Hiyama (CO−H) coupling of aryl triazenes using phenyl boronic acid and triethoxy(phenyl)silane respectively via a Pd‐catalysis in combination with Ionic liquids (ILs). Four different ILs have been employed as solvent/reagent/promotor(s) to afford the targeted products in reasonably good yields. As per the predictive mechanism, an in situ generated N‐Heterocarbene‐Ionicliquid‐Palladium (NHC‐IL‐Pd) species serve as a regenerative catalyst while the N‐formyl saccharin (NFSac), a non‐hazardous and commercially available crystalline compound was used as carbon monoxide (CO) surrogate playing important roles to accomplish the desired products in good yields.
The carbonylative Suzuki and Hiyama cross‐coupling reactions, by employing triazenes as new coupling partners and N‐Formyl Saccharin as carbon monoxide (CO) surrogate in ionic liquids. A protocol was tested that uses ILs as the solvent, Brønsted‐acid or promoter, fluoride ion source and recyclable IL. |
doi_str_mv | 10.1002/slct.202300871 |
format | Article |
fullrecord | <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_slct_202300871</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>SLCT202300871</sourcerecordid><originalsourceid>FETCH-LOGICAL-c2891-6a44c04b7799ecbc496aa0ad25c0cc4211fc8167af7245b9256f8bd77238fa763</originalsourceid><addsrcrecordid>eNqFkMFOwkAQhhujiQS5ep4XAHeXdrf1hkTUhMgBPDfTYasrZUt2W009-Qg-js_jk0jBoDdPM5P5_38mXxCcczbgjIkLX1A1EEwMGYsVPwo6YiijvozC5PhPfxr0vH9mjHEZSxGpTvA5ggmSKTT4xlZP2hsPZQ5XBl1TwEpXpdUejAWnqaECs53SV3p9CQtn8E23e_Rg9StQWW8KYx9hg66y2u2M21AgdFlpmwIr86JhXr_VKwNol3BrGlwjkCu9_3r_OAQ4jVSZ0nqofTvfT-ZI7ZnxDHxZO9JnwUmOhde9n9oNHibXi_Ftfzq7uRuPpn0SccL7EsOQWJgplSSaMgoTichwKSJiRKHgPKeYS4W5EmGUJSKSeZwtlRLDOEclh91gsM_d_eh0nm6cWW_ppJylLfq0RZ8e0G8Nyd7wuqXa_KNO59Px4tf7DcPDjaM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A Facile synthesis of Biaryl ketones in recyclable system: Triazenes as new coupling partners in the carbonylative Suzuki and Hiyama cross‐coupling reactions using NFSac as CO source</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Anchi, Athmanand ; Kalkhambkar, Rajesh G. ; Kumar P, Pavan ; Naik, Ravi S ; Refat, Moamen S. ; Adam, Abdel Majid A. ; Alsuhaibani, Amnah Mohammed ; Bakare, Safyah B.</creator><creatorcontrib>Anchi, Athmanand ; Kalkhambkar, Rajesh G. ; Kumar P, Pavan ; Naik, Ravi S ; Refat, Moamen S. ; Adam, Abdel Majid A. ; Alsuhaibani, Amnah Mohammed ; Bakare, Safyah B.</creatorcontrib><description>Palladium‐catalyzed carbonylation reactions aid as potent tools for the insertion of carbonyl unit(s) in a wide array of molecules possessing vast number of applications in multiple domains. An efficient and facile protocol has been reported for the carbonylative Suzuki (CO−S) and carbonylative Hiyama (CO−H) coupling of aryl triazenes using phenyl boronic acid and triethoxy(phenyl)silane respectively via a Pd‐catalysis in combination with Ionic liquids (ILs). Four different ILs have been employed as solvent/reagent/promotor(s) to afford the targeted products in reasonably good yields. As per the predictive mechanism, an in situ generated N‐Heterocarbene‐Ionicliquid‐Palladium (NHC‐IL‐Pd) species serve as a regenerative catalyst while the N‐formyl saccharin (NFSac), a non‐hazardous and commercially available crystalline compound was used as carbon monoxide (CO) surrogate playing important roles to accomplish the desired products in good yields.
The carbonylative Suzuki and Hiyama cross‐coupling reactions, by employing triazenes as new coupling partners and N‐Formyl Saccharin as carbon monoxide (CO) surrogate in ionic liquids. A protocol was tested that uses ILs as the solvent, Brønsted‐acid or promoter, fluoride ion source and recyclable IL.</description><identifier>ISSN: 2365-6549</identifier><identifier>EISSN: 2365-6549</identifier><identifier>DOI: 10.1002/slct.202300871</identifier><language>eng</language><subject>Cabonylative Suzuki and Hiyama cross-coupling ; In situ Cabonylative protocol ; Ionic Liquids ; N-Formyl Saccharin</subject><ispartof>ChemistrySelect (Weinheim), 2023-06, Vol.8 (23), p.n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2891-6a44c04b7799ecbc496aa0ad25c0cc4211fc8167af7245b9256f8bd77238fa763</citedby><cites>FETCH-LOGICAL-c2891-6a44c04b7799ecbc496aa0ad25c0cc4211fc8167af7245b9256f8bd77238fa763</cites><orcidid>0000-0003-2821-6949</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%2Fslct.202300871$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fslct.202300871$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Anchi, Athmanand</creatorcontrib><creatorcontrib>Kalkhambkar, Rajesh G.</creatorcontrib><creatorcontrib>Kumar P, Pavan</creatorcontrib><creatorcontrib>Naik, Ravi S</creatorcontrib><creatorcontrib>Refat, Moamen S.</creatorcontrib><creatorcontrib>Adam, Abdel Majid A.</creatorcontrib><creatorcontrib>Alsuhaibani, Amnah Mohammed</creatorcontrib><creatorcontrib>Bakare, Safyah B.</creatorcontrib><title>A Facile synthesis of Biaryl ketones in recyclable system: Triazenes as new coupling partners in the carbonylative Suzuki and Hiyama cross‐coupling reactions using NFSac as CO source</title><title>ChemistrySelect (Weinheim)</title><description>Palladium‐catalyzed carbonylation reactions aid as potent tools for the insertion of carbonyl unit(s) in a wide array of molecules possessing vast number of applications in multiple domains. An efficient and facile protocol has been reported for the carbonylative Suzuki (CO−S) and carbonylative Hiyama (CO−H) coupling of aryl triazenes using phenyl boronic acid and triethoxy(phenyl)silane respectively via a Pd‐catalysis in combination with Ionic liquids (ILs). Four different ILs have been employed as solvent/reagent/promotor(s) to afford the targeted products in reasonably good yields. As per the predictive mechanism, an in situ generated N‐Heterocarbene‐Ionicliquid‐Palladium (NHC‐IL‐Pd) species serve as a regenerative catalyst while the N‐formyl saccharin (NFSac), a non‐hazardous and commercially available crystalline compound was used as carbon monoxide (CO) surrogate playing important roles to accomplish the desired products in good yields.
The carbonylative Suzuki and Hiyama cross‐coupling reactions, by employing triazenes as new coupling partners and N‐Formyl Saccharin as carbon monoxide (CO) surrogate in ionic liquids. A protocol was tested that uses ILs as the solvent, Brønsted‐acid or promoter, fluoride ion source and recyclable IL.</description><subject>Cabonylative Suzuki and Hiyama cross-coupling</subject><subject>In situ Cabonylative protocol</subject><subject>Ionic Liquids</subject><subject>N-Formyl Saccharin</subject><issn>2365-6549</issn><issn>2365-6549</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkMFOwkAQhhujiQS5ep4XAHeXdrf1hkTUhMgBPDfTYasrZUt2W009-Qg-js_jk0jBoDdPM5P5_38mXxCcczbgjIkLX1A1EEwMGYsVPwo6YiijvozC5PhPfxr0vH9mjHEZSxGpTvA5ggmSKTT4xlZP2hsPZQ5XBl1TwEpXpdUejAWnqaECs53SV3p9CQtn8E23e_Rg9StQWW8KYx9hg66y2u2M21AgdFlpmwIr86JhXr_VKwNol3BrGlwjkCu9_3r_OAQ4jVSZ0nqofTvfT-ZI7ZnxDHxZO9JnwUmOhde9n9oNHibXi_Ftfzq7uRuPpn0SccL7EsOQWJgplSSaMgoTichwKSJiRKHgPKeYS4W5EmGUJSKSeZwtlRLDOEclh91gsM_d_eh0nm6cWW_ppJylLfq0RZ8e0G8Nyd7wuqXa_KNO59Px4tf7DcPDjaM</recordid><startdate>20230620</startdate><enddate>20230620</enddate><creator>Anchi, Athmanand</creator><creator>Kalkhambkar, Rajesh G.</creator><creator>Kumar P, Pavan</creator><creator>Naik, Ravi S</creator><creator>Refat, Moamen S.</creator><creator>Adam, Abdel Majid A.</creator><creator>Alsuhaibani, Amnah Mohammed</creator><creator>Bakare, Safyah B.</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2821-6949</orcidid></search><sort><creationdate>20230620</creationdate><title>A Facile synthesis of Biaryl ketones in recyclable system: Triazenes as new coupling partners in the carbonylative Suzuki and Hiyama cross‐coupling reactions using NFSac as CO source</title><author>Anchi, Athmanand ; Kalkhambkar, Rajesh G. ; Kumar P, Pavan ; Naik, Ravi S ; Refat, Moamen S. ; Adam, Abdel Majid A. ; Alsuhaibani, Amnah Mohammed ; Bakare, Safyah B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2891-6a44c04b7799ecbc496aa0ad25c0cc4211fc8167af7245b9256f8bd77238fa763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Cabonylative Suzuki and Hiyama cross-coupling</topic><topic>In situ Cabonylative protocol</topic><topic>Ionic Liquids</topic><topic>N-Formyl Saccharin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Anchi, Athmanand</creatorcontrib><creatorcontrib>Kalkhambkar, Rajesh G.</creatorcontrib><creatorcontrib>Kumar P, Pavan</creatorcontrib><creatorcontrib>Naik, Ravi S</creatorcontrib><creatorcontrib>Refat, Moamen S.</creatorcontrib><creatorcontrib>Adam, Abdel Majid A.</creatorcontrib><creatorcontrib>Alsuhaibani, Amnah Mohammed</creatorcontrib><creatorcontrib>Bakare, Safyah B.</creatorcontrib><collection>CrossRef</collection><jtitle>ChemistrySelect (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Anchi, Athmanand</au><au>Kalkhambkar, Rajesh G.</au><au>Kumar P, Pavan</au><au>Naik, Ravi S</au><au>Refat, Moamen S.</au><au>Adam, Abdel Majid A.</au><au>Alsuhaibani, Amnah Mohammed</au><au>Bakare, Safyah B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Facile synthesis of Biaryl ketones in recyclable system: Triazenes as new coupling partners in the carbonylative Suzuki and Hiyama cross‐coupling reactions using NFSac as CO source</atitle><jtitle>ChemistrySelect (Weinheim)</jtitle><date>2023-06-20</date><risdate>2023</risdate><volume>8</volume><issue>23</issue><epage>n/a</epage><issn>2365-6549</issn><eissn>2365-6549</eissn><abstract>Palladium‐catalyzed carbonylation reactions aid as potent tools for the insertion of carbonyl unit(s) in a wide array of molecules possessing vast number of applications in multiple domains. An efficient and facile protocol has been reported for the carbonylative Suzuki (CO−S) and carbonylative Hiyama (CO−H) coupling of aryl triazenes using phenyl boronic acid and triethoxy(phenyl)silane respectively via a Pd‐catalysis in combination with Ionic liquids (ILs). Four different ILs have been employed as solvent/reagent/promotor(s) to afford the targeted products in reasonably good yields. As per the predictive mechanism, an in situ generated N‐Heterocarbene‐Ionicliquid‐Palladium (NHC‐IL‐Pd) species serve as a regenerative catalyst while the N‐formyl saccharin (NFSac), a non‐hazardous and commercially available crystalline compound was used as carbon monoxide (CO) surrogate playing important roles to accomplish the desired products in good yields.
The carbonylative Suzuki and Hiyama cross‐coupling reactions, by employing triazenes as new coupling partners and N‐Formyl Saccharin as carbon monoxide (CO) surrogate in ionic liquids. A protocol was tested that uses ILs as the solvent, Brønsted‐acid or promoter, fluoride ion source and recyclable IL.</abstract><doi>10.1002/slct.202300871</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0003-2821-6949</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 2365-6549 |
ispartof | ChemistrySelect (Weinheim), 2023-06, Vol.8 (23), p.n/a |
issn | 2365-6549 2365-6549 |
language | eng |
recordid | cdi_crossref_primary_10_1002_slct_202300871 |
source | Wiley Online Library Journals Frontfile Complete |
subjects | Cabonylative Suzuki and Hiyama cross-coupling In situ Cabonylative protocol Ionic Liquids N-Formyl Saccharin |
title | A Facile synthesis of Biaryl ketones in recyclable system: Triazenes as new coupling partners in the carbonylative Suzuki and Hiyama cross‐coupling reactions using NFSac as CO source |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T06%3A36%3A48IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Facile%20synthesis%20of%20Biaryl%20ketones%20in%20recyclable%20system:%20Triazenes%20as%20new%20coupling%20partners%20in%20the%20carbonylative%20Suzuki%20and%20Hiyama%20cross%E2%80%90coupling%20reactions%20using%20NFSac%20as%20CO%20source&rft.jtitle=ChemistrySelect%20(Weinheim)&rft.au=Anchi,%20Athmanand&rft.date=2023-06-20&rft.volume=8&rft.issue=23&rft.epage=n/a&rft.issn=2365-6549&rft.eissn=2365-6549&rft_id=info:doi/10.1002/slct.202300871&rft_dat=%3Cwiley_cross%3ESLCT202300871%3C/wiley_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |