Oxidative Alkoxycarbonylation of Alkynes by Means of Aryl α-Diimine Palladium(II) Complexes as Catalysts

The straightforward in situ synthesized bis(2,6‐diisopropyl)acenaphthenequinonediimine palladium triflate catalyst was generally employed for both the mono‐alkoxycarbonylation of terminal alkynes, and the bis‐alkoxycarbonylation of 1,2‐disubstituted alkynes by using mild reaction conditions [carbon...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Advanced synthesis & catalysis 2016-10, Vol.358 (20), p.3244-3253
Hauptverfasser: Beltrani, Michela, Carfagna, Carla, Milani, Barbara, Mancuso, Raffaella, Gabriele, Bartolo, Fini, Francesco
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3253
container_issue 20
container_start_page 3244
container_title Advanced synthesis & catalysis
container_volume 358
creator Beltrani, Michela
Carfagna, Carla
Milani, Barbara
Mancuso, Raffaella
Gabriele, Bartolo
Fini, Francesco
description The straightforward in situ synthesized bis(2,6‐diisopropyl)acenaphthenequinonediimine palladium triflate catalyst was generally employed for both the mono‐alkoxycarbonylation of terminal alkynes, and the bis‐alkoxycarbonylation of 1,2‐disubstituted alkynes by using mild reaction conditions [carbon monoxide pressure (PCO)=4 bar, temperature=20 °C]. Utilizing low catalyst loading (down to 0.5 mol%), a variety of propiolic esters were synthesized with good to excellent isolated yields. Most importantly the system was very efficient not only with methanol but also with a range of different alcohols, starting from the less hindered benzyl alcohol to the most hindered ones, such as isopropyl alcohol and tert‐butyl alcohol. In addition, aromatic and aliphatic 1,2‐disubstituted alkynes were converted into maleic acid derivatives, together with an acid‐catalyzed isomerization reaction, showing modest to good selectivity and excellent combined yields. In particular 3‐hexyne showed a satisfactory degree of selectivity for the maleic diesters of methanol and benzyl alcohol, obtaining the corresponding products with good isolated yields.
doi_str_mv 10.1002/adsc.201600521
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1845814960</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1845814960</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4001-c93a9ff3fdf624efbbf8b5c59646ca03f47e8685e35e2a5ff6eb299792dae4333</originalsourceid><addsrcrecordid>eNqFkM1OwkAUhRujiYhuXXeJi-JM56edJSmKJAgmYFxOpu2dZGTaYqcofSxfxGeyiCHuXN2Tk_PdnBzPu8ZoiBEKb1XusmGIMEeIhfjE62GOWUAxF6dHzdC5d-HcK0I4iqOo55nFzuSqMe_gj-y62rWZqtOqbG3nVaVf6b3dluD8tPUfQZXux6tb6399BmNjClOC_6SsVbnZFoPp9MZPqmJjYdcxyvmJapRtXeMuvTOtrIOr39v3nu_vVslDMFtMpsloFmS0axVkgiihNdG55iEFnaY6TlnGBKc8U4hoGkHMYwaEQaiY1hzSUIhIhLkCSgjpe4PD301dvW3BNbIwLoOuYAnV1kkcUxZjKjjqosNDNKsr52rQclObQtWtxEjuN5X7TeVx0w4QB-DDWGj_ScvReJn8ZYMDa1wDuyOr6rXkEYmYfJlPJFsJNmdjKpfkG2YEi8Q</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1845814960</pqid></control><display><type>article</type><title>Oxidative Alkoxycarbonylation of Alkynes by Means of Aryl α-Diimine Palladium(II) Complexes as Catalysts</title><source>Wiley Online Library All Journals</source><creator>Beltrani, Michela ; Carfagna, Carla ; Milani, Barbara ; Mancuso, Raffaella ; Gabriele, Bartolo ; Fini, Francesco</creator><creatorcontrib>Beltrani, Michela ; Carfagna, Carla ; Milani, Barbara ; Mancuso, Raffaella ; Gabriele, Bartolo ; Fini, Francesco</creatorcontrib><description>The straightforward in situ synthesized bis(2,6‐diisopropyl)acenaphthenequinonediimine palladium triflate catalyst was generally employed for both the mono‐alkoxycarbonylation of terminal alkynes, and the bis‐alkoxycarbonylation of 1,2‐disubstituted alkynes by using mild reaction conditions [carbon monoxide pressure (PCO)=4 bar, temperature=20 °C]. Utilizing low catalyst loading (down to 0.5 mol%), a variety of propiolic esters were synthesized with good to excellent isolated yields. Most importantly the system was very efficient not only with methanol but also with a range of different alcohols, starting from the less hindered benzyl alcohol to the most hindered ones, such as isopropyl alcohol and tert‐butyl alcohol. In addition, aromatic and aliphatic 1,2‐disubstituted alkynes were converted into maleic acid derivatives, together with an acid‐catalyzed isomerization reaction, showing modest to good selectivity and excellent combined yields. In particular 3‐hexyne showed a satisfactory degree of selectivity for the maleic diesters of methanol and benzyl alcohol, obtaining the corresponding products with good isolated yields.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201600521</identifier><language>eng</language><publisher>Blackwell Publishing Ltd</publisher><subject>Alcohols ; Alkynes ; aryl α-diimine ligands ; Benzyl alcohol ; carbonylation ; Catalysis ; Catalysts ; maleic acid esters ; Methyl alcohol ; oxidative carbonylation ; palladium ; propiolic acid esters ; Selectivity ; Synthesis (chemistry)</subject><ispartof>Advanced synthesis &amp; catalysis, 2016-10, Vol.358 (20), p.3244-3253</ispartof><rights>2016 Wiley‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4001-c93a9ff3fdf624efbbf8b5c59646ca03f47e8685e35e2a5ff6eb299792dae4333</citedby><cites>FETCH-LOGICAL-c4001-c93a9ff3fdf624efbbf8b5c59646ca03f47e8685e35e2a5ff6eb299792dae4333</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.201600521$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201600521$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Beltrani, Michela</creatorcontrib><creatorcontrib>Carfagna, Carla</creatorcontrib><creatorcontrib>Milani, Barbara</creatorcontrib><creatorcontrib>Mancuso, Raffaella</creatorcontrib><creatorcontrib>Gabriele, Bartolo</creatorcontrib><creatorcontrib>Fini, Francesco</creatorcontrib><title>Oxidative Alkoxycarbonylation of Alkynes by Means of Aryl α-Diimine Palladium(II) Complexes as Catalysts</title><title>Advanced synthesis &amp; catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>The straightforward in situ synthesized bis(2,6‐diisopropyl)acenaphthenequinonediimine palladium triflate catalyst was generally employed for both the mono‐alkoxycarbonylation of terminal alkynes, and the bis‐alkoxycarbonylation of 1,2‐disubstituted alkynes by using mild reaction conditions [carbon monoxide pressure (PCO)=4 bar, temperature=20 °C]. Utilizing low catalyst loading (down to 0.5 mol%), a variety of propiolic esters were synthesized with good to excellent isolated yields. Most importantly the system was very efficient not only with methanol but also with a range of different alcohols, starting from the less hindered benzyl alcohol to the most hindered ones, such as isopropyl alcohol and tert‐butyl alcohol. In addition, aromatic and aliphatic 1,2‐disubstituted alkynes were converted into maleic acid derivatives, together with an acid‐catalyzed isomerization reaction, showing modest to good selectivity and excellent combined yields. In particular 3‐hexyne showed a satisfactory degree of selectivity for the maleic diesters of methanol and benzyl alcohol, obtaining the corresponding products with good isolated yields.</description><subject>Alcohols</subject><subject>Alkynes</subject><subject>aryl α-diimine ligands</subject><subject>Benzyl alcohol</subject><subject>carbonylation</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>maleic acid esters</subject><subject>Methyl alcohol</subject><subject>oxidative carbonylation</subject><subject>palladium</subject><subject>propiolic acid esters</subject><subject>Selectivity</subject><subject>Synthesis (chemistry)</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkM1OwkAUhRujiYhuXXeJi-JM56edJSmKJAgmYFxOpu2dZGTaYqcofSxfxGeyiCHuXN2Tk_PdnBzPu8ZoiBEKb1XusmGIMEeIhfjE62GOWUAxF6dHzdC5d-HcK0I4iqOo55nFzuSqMe_gj-y62rWZqtOqbG3nVaVf6b3dluD8tPUfQZXux6tb6399BmNjClOC_6SsVbnZFoPp9MZPqmJjYdcxyvmJapRtXeMuvTOtrIOr39v3nu_vVslDMFtMpsloFmS0axVkgiihNdG55iEFnaY6TlnGBKc8U4hoGkHMYwaEQaiY1hzSUIhIhLkCSgjpe4PD301dvW3BNbIwLoOuYAnV1kkcUxZjKjjqosNDNKsr52rQclObQtWtxEjuN5X7TeVx0w4QB-DDWGj_ScvReJn8ZYMDa1wDuyOr6rXkEYmYfJlPJFsJNmdjKpfkG2YEi8Q</recordid><startdate>20161020</startdate><enddate>20161020</enddate><creator>Beltrani, Michela</creator><creator>Carfagna, Carla</creator><creator>Milani, Barbara</creator><creator>Mancuso, Raffaella</creator><creator>Gabriele, Bartolo</creator><creator>Fini, Francesco</creator><general>Blackwell Publishing Ltd</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20161020</creationdate><title>Oxidative Alkoxycarbonylation of Alkynes by Means of Aryl α-Diimine Palladium(II) Complexes as Catalysts</title><author>Beltrani, Michela ; Carfagna, Carla ; Milani, Barbara ; Mancuso, Raffaella ; Gabriele, Bartolo ; Fini, Francesco</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4001-c93a9ff3fdf624efbbf8b5c59646ca03f47e8685e35e2a5ff6eb299792dae4333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Alcohols</topic><topic>Alkynes</topic><topic>aryl α-diimine ligands</topic><topic>Benzyl alcohol</topic><topic>carbonylation</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>maleic acid esters</topic><topic>Methyl alcohol</topic><topic>oxidative carbonylation</topic><topic>palladium</topic><topic>propiolic acid esters</topic><topic>Selectivity</topic><topic>Synthesis (chemistry)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Beltrani, Michela</creatorcontrib><creatorcontrib>Carfagna, Carla</creatorcontrib><creatorcontrib>Milani, Barbara</creatorcontrib><creatorcontrib>Mancuso, Raffaella</creatorcontrib><creatorcontrib>Gabriele, Bartolo</creatorcontrib><creatorcontrib>Fini, Francesco</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Beltrani, Michela</au><au>Carfagna, Carla</au><au>Milani, Barbara</au><au>Mancuso, Raffaella</au><au>Gabriele, Bartolo</au><au>Fini, Francesco</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative Alkoxycarbonylation of Alkynes by Means of Aryl α-Diimine Palladium(II) Complexes as Catalysts</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2016-10-20</date><risdate>2016</risdate><volume>358</volume><issue>20</issue><spage>3244</spage><epage>3253</epage><pages>3244-3253</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The straightforward in situ synthesized bis(2,6‐diisopropyl)acenaphthenequinonediimine palladium triflate catalyst was generally employed for both the mono‐alkoxycarbonylation of terminal alkynes, and the bis‐alkoxycarbonylation of 1,2‐disubstituted alkynes by using mild reaction conditions [carbon monoxide pressure (PCO)=4 bar, temperature=20 °C]. Utilizing low catalyst loading (down to 0.5 mol%), a variety of propiolic esters were synthesized with good to excellent isolated yields. Most importantly the system was very efficient not only with methanol but also with a range of different alcohols, starting from the less hindered benzyl alcohol to the most hindered ones, such as isopropyl alcohol and tert‐butyl alcohol. In addition, aromatic and aliphatic 1,2‐disubstituted alkynes were converted into maleic acid derivatives, together with an acid‐catalyzed isomerization reaction, showing modest to good selectivity and excellent combined yields. In particular 3‐hexyne showed a satisfactory degree of selectivity for the maleic diesters of methanol and benzyl alcohol, obtaining the corresponding products with good isolated yields.</abstract><pub>Blackwell Publishing Ltd</pub><doi>10.1002/adsc.201600521</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2016-10, Vol.358 (20), p.3244-3253
issn 1615-4150
1615-4169
language eng
recordid cdi_proquest_miscellaneous_1845814960
source Wiley Online Library All Journals
subjects Alcohols
Alkynes
aryl α-diimine ligands
Benzyl alcohol
carbonylation
Catalysis
Catalysts
maleic acid esters
Methyl alcohol
oxidative carbonylation
palladium
propiolic acid esters
Selectivity
Synthesis (chemistry)
title Oxidative Alkoxycarbonylation of Alkynes by Means of Aryl α-Diimine Palladium(II) Complexes as Catalysts
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T10%3A43%3A51IST&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=Oxidative%20Alkoxycarbonylation%20of%20Alkynes%20by%20Means%20of%20Aryl%20%CE%B1-Diimine%20Palladium(II)%20Complexes%20as%20Catalysts&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Beltrani,%20Michela&rft.date=2016-10-20&rft.volume=358&rft.issue=20&rft.spage=3244&rft.epage=3253&rft.pages=3244-3253&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201600521&rft_dat=%3Cproquest_cross%3E1845814960%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=1845814960&rft_id=info:pmid/&rfr_iscdi=true