Palladium-Catalyzed Carbonylation for General Synthesis of Aurones Using CO 2

The carbonylation of alkynes using CO to generate aurones is to date unknown. In this study, a palladium-catalyzed carbonylation of terminal aromatic alkynes and the waste hydrosilane, poly(methylhydrosiloxane) (PMHS), is carried out with 2-iodophenol using CO to produce aurones. A variety of termin...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:ChemSusChem 2023-05, Vol.16 (10), p.e202202365
Hauptverfasser: Huang, Zijun, Li, Yudong, Zhou, Jiaxing, Zhang, Yi, Wu, Jiacheng, Wu, Yongkai, Zhang, Fan, Fang, Zhengjun, Li, Yuehui
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page
container_issue 10
container_start_page e202202365
container_title ChemSusChem
container_volume 16
creator Huang, Zijun
Li, Yudong
Zhou, Jiaxing
Zhang, Yi
Wu, Jiacheng
Wu, Yongkai
Zhang, Fan
Fang, Zhengjun
Li, Yuehui
description The carbonylation of alkynes using CO to generate aurones is to date unknown. In this study, a palladium-catalyzed carbonylation of terminal aromatic alkynes and the waste hydrosilane, poly(methylhydrosiloxane) (PMHS), is carried out with 2-iodophenol using CO to produce aurones. A variety of terminal alkynes and substituted 2-iodophenols are transformed into aurones in good yields. Preliminary mechanistic studies indicate that silyl formate, generated from CO and PMHS, plays a crucial role in the carbonylation reaction.
doi_str_mv 10.1002/cssc.202202365
format Article
fullrecord <record><control><sourceid>pubmed_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_cssc_202202365</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>36737418</sourcerecordid><originalsourceid>FETCH-LOGICAL-c1078-b356b65075d6b5400b1733a820214304a3ba47dc0ebc4e8fc1f1cea416fa8b073</originalsourceid><addsrcrecordid>eNo9kF1LwzAUhoMobk5vvZT8gdaTJk3q5Sg6hckEHXhXTtJEK_0YSXtRf_06poMXzntxngPnIeSWQcwAknsTgokTSKZwmZ6ROcukiFIpPs9PnbMZuQrhB0DCg5SXZMal4kqwbE5e37CusayGJsqxx3r8tSXN0euuHWvsq66lrvN0ZVvrsabvY9t_21AF2jm6HHzX2kC3oWq_aL6hyTW5cFgHe_M3F2T79PiRP0frzeolX64jw0Blkeap1DIFlZZSpwJAM8U5ZtMTTHAQyDUKVRqw2gibOcMcMxYFkw4zDYovSHy8a3wXgreu2PmqQT8WDIqDl-LgpTh5mYC7I7AbdGPL0_q_CL4Hg-VeEQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Palladium-Catalyzed Carbonylation for General Synthesis of Aurones Using CO 2</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Huang, Zijun ; Li, Yudong ; Zhou, Jiaxing ; Zhang, Yi ; Wu, Jiacheng ; Wu, Yongkai ; Zhang, Fan ; Fang, Zhengjun ; Li, Yuehui</creator><creatorcontrib>Huang, Zijun ; Li, Yudong ; Zhou, Jiaxing ; Zhang, Yi ; Wu, Jiacheng ; Wu, Yongkai ; Zhang, Fan ; Fang, Zhengjun ; Li, Yuehui</creatorcontrib><description>The carbonylation of alkynes using CO to generate aurones is to date unknown. In this study, a palladium-catalyzed carbonylation of terminal aromatic alkynes and the waste hydrosilane, poly(methylhydrosiloxane) (PMHS), is carried out with 2-iodophenol using CO to produce aurones. A variety of terminal alkynes and substituted 2-iodophenols are transformed into aurones in good yields. Preliminary mechanistic studies indicate that silyl formate, generated from CO and PMHS, plays a crucial role in the carbonylation reaction.</description><identifier>ISSN: 1864-5631</identifier><identifier>EISSN: 1864-564X</identifier><identifier>DOI: 10.1002/cssc.202202365</identifier><identifier>PMID: 36737418</identifier><language>eng</language><publisher>Germany</publisher><ispartof>ChemSusChem, 2023-05, Vol.16 (10), p.e202202365</ispartof><rights>2023 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1078-b356b65075d6b5400b1733a820214304a3ba47dc0ebc4e8fc1f1cea416fa8b073</citedby><cites>FETCH-LOGICAL-c1078-b356b65075d6b5400b1733a820214304a3ba47dc0ebc4e8fc1f1cea416fa8b073</cites><orcidid>0000-0002-4520-1418 ; 0000-0002-6038-4320</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/36737418$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huang, Zijun</creatorcontrib><creatorcontrib>Li, Yudong</creatorcontrib><creatorcontrib>Zhou, Jiaxing</creatorcontrib><creatorcontrib>Zhang, Yi</creatorcontrib><creatorcontrib>Wu, Jiacheng</creatorcontrib><creatorcontrib>Wu, Yongkai</creatorcontrib><creatorcontrib>Zhang, Fan</creatorcontrib><creatorcontrib>Fang, Zhengjun</creatorcontrib><creatorcontrib>Li, Yuehui</creatorcontrib><title>Palladium-Catalyzed Carbonylation for General Synthesis of Aurones Using CO 2</title><title>ChemSusChem</title><addtitle>ChemSusChem</addtitle><description>The carbonylation of alkynes using CO to generate aurones is to date unknown. In this study, a palladium-catalyzed carbonylation of terminal aromatic alkynes and the waste hydrosilane, poly(methylhydrosiloxane) (PMHS), is carried out with 2-iodophenol using CO to produce aurones. A variety of terminal alkynes and substituted 2-iodophenols are transformed into aurones in good yields. Preliminary mechanistic studies indicate that silyl formate, generated from CO and PMHS, plays a crucial role in the carbonylation reaction.</description><issn>1864-5631</issn><issn>1864-564X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNo9kF1LwzAUhoMobk5vvZT8gdaTJk3q5Sg6hckEHXhXTtJEK_0YSXtRf_06poMXzntxngPnIeSWQcwAknsTgokTSKZwmZ6ROcukiFIpPs9PnbMZuQrhB0DCg5SXZMal4kqwbE5e37CusayGJsqxx3r8tSXN0euuHWvsq66lrvN0ZVvrsabvY9t_21AF2jm6HHzX2kC3oWq_aL6hyTW5cFgHe_M3F2T79PiRP0frzeolX64jw0Blkeap1DIFlZZSpwJAM8U5ZtMTTHAQyDUKVRqw2gibOcMcMxYFkw4zDYovSHy8a3wXgreu2PmqQT8WDIqDl-LgpTh5mYC7I7AbdGPL0_q_CL4Hg-VeEQ</recordid><startdate>20230519</startdate><enddate>20230519</enddate><creator>Huang, Zijun</creator><creator>Li, Yudong</creator><creator>Zhou, Jiaxing</creator><creator>Zhang, Yi</creator><creator>Wu, Jiacheng</creator><creator>Wu, Yongkai</creator><creator>Zhang, Fan</creator><creator>Fang, Zhengjun</creator><creator>Li, Yuehui</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-4520-1418</orcidid><orcidid>https://orcid.org/0000-0002-6038-4320</orcidid></search><sort><creationdate>20230519</creationdate><title>Palladium-Catalyzed Carbonylation for General Synthesis of Aurones Using CO 2</title><author>Huang, Zijun ; Li, Yudong ; Zhou, Jiaxing ; Zhang, Yi ; Wu, Jiacheng ; Wu, Yongkai ; Zhang, Fan ; Fang, Zhengjun ; Li, Yuehui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1078-b356b65075d6b5400b1733a820214304a3ba47dc0ebc4e8fc1f1cea416fa8b073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Zijun</creatorcontrib><creatorcontrib>Li, Yudong</creatorcontrib><creatorcontrib>Zhou, Jiaxing</creatorcontrib><creatorcontrib>Zhang, Yi</creatorcontrib><creatorcontrib>Wu, Jiacheng</creatorcontrib><creatorcontrib>Wu, Yongkai</creatorcontrib><creatorcontrib>Zhang, Fan</creatorcontrib><creatorcontrib>Fang, Zhengjun</creatorcontrib><creatorcontrib>Li, Yuehui</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>ChemSusChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Zijun</au><au>Li, Yudong</au><au>Zhou, Jiaxing</au><au>Zhang, Yi</au><au>Wu, Jiacheng</au><au>Wu, Yongkai</au><au>Zhang, Fan</au><au>Fang, Zhengjun</au><au>Li, Yuehui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Carbonylation for General Synthesis of Aurones Using CO 2</atitle><jtitle>ChemSusChem</jtitle><addtitle>ChemSusChem</addtitle><date>2023-05-19</date><risdate>2023</risdate><volume>16</volume><issue>10</issue><spage>e202202365</spage><pages>e202202365-</pages><issn>1864-5631</issn><eissn>1864-564X</eissn><abstract>The carbonylation of alkynes using CO to generate aurones is to date unknown. In this study, a palladium-catalyzed carbonylation of terminal aromatic alkynes and the waste hydrosilane, poly(methylhydrosiloxane) (PMHS), is carried out with 2-iodophenol using CO to produce aurones. A variety of terminal alkynes and substituted 2-iodophenols are transformed into aurones in good yields. Preliminary mechanistic studies indicate that silyl formate, generated from CO and PMHS, plays a crucial role in the carbonylation reaction.</abstract><cop>Germany</cop><pmid>36737418</pmid><doi>10.1002/cssc.202202365</doi><orcidid>https://orcid.org/0000-0002-4520-1418</orcidid><orcidid>https://orcid.org/0000-0002-6038-4320</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1864-5631
ispartof ChemSusChem, 2023-05, Vol.16 (10), p.e202202365
issn 1864-5631
1864-564X
language eng
recordid cdi_crossref_primary_10_1002_cssc_202202365
source Wiley Online Library Journals Frontfile Complete
title Palladium-Catalyzed Carbonylation for General Synthesis of Aurones Using CO 2
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-27T18%3A23%3A20IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Palladium-Catalyzed%20Carbonylation%20for%20General%20Synthesis%20of%20Aurones%20Using%20CO%202&rft.jtitle=ChemSusChem&rft.au=Huang,%20Zijun&rft.date=2023-05-19&rft.volume=16&rft.issue=10&rft.spage=e202202365&rft.pages=e202202365-&rft.issn=1864-5631&rft.eissn=1864-564X&rft_id=info:doi/10.1002/cssc.202202365&rft_dat=%3Cpubmed_cross%3E36737418%3C/pubmed_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/36737418&rfr_iscdi=true