Solid acids as cocatalysts in the chelation-assisted hydroacylation of alkenes and alkynes
The use of homogeneous Brønsted acid cocatalysts (such as benzoic acid) in hydroacylation reactions via imine intermediates has been extensively studied. However, the use of heterogeneous cocatalysts has been limited to montmorillonite K10. Thus, we can use other solid acids to increase the efficien...
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| Veröffentlicht in: | RSC advances 2024-10, Vol.14 (43), p.31675-31682 |
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| creator | Vergara-Arenas, Blanca I García-Ríos, Eréndira Gaviño, Rubén Cárdenas, Jorge Martinez-Garcia, Alfredo Juarez-Arellano, Erick A López-Torres, Adolfo Morales-Serna, José A |
| description | The use of homogeneous Brønsted acid cocatalysts (such as benzoic acid) in hydroacylation reactions
via
imine intermediates has been extensively studied. However, the use of heterogeneous cocatalysts has been limited to montmorillonite K10. Thus, we can use other solid acids to increase the efficiency of the reaction. In this study, we describe the effects of sulfated zirconia, Al-MCM-41 or superacid modified montmorillonite on the hydroacylation of alkenes and alkynes with aldehydes
via
imine intermediates and in the presence of the Wilkinson complex. Furthermore, we addressed the dual role of montmorillonite, a redox reagent in the presence of TEMPO and an acid solid, allowing the direct use of benzyl alcohols as substrates to generate saturated or α,β-unsaturated ketones.
Hydroacylation of alkenes and alkynes in the presence of solid acids. |
| doi_str_mv | 10.1039/d4ra05791k |
| format | Article |
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via
imine intermediates has been extensively studied. However, the use of heterogeneous cocatalysts has been limited to montmorillonite K10. Thus, we can use other solid acids to increase the efficiency of the reaction. In this study, we describe the effects of sulfated zirconia, Al-MCM-41 or superacid modified montmorillonite on the hydroacylation of alkenes and alkynes with aldehydes
via
imine intermediates and in the presence of the Wilkinson complex. Furthermore, we addressed the dual role of montmorillonite, a redox reagent in the presence of TEMPO and an acid solid, allowing the direct use of benzyl alcohols as substrates to generate saturated or α,β-unsaturated ketones.
Hydroacylation of alkenes and alkynes in the presence of solid acids.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d4ra05791k</identifier><identifier>PMID: 39376529</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes ; Alkenes ; Alkynes ; Benzoic acid ; Benzyl alcohol ; Chelation ; Chemistry ; Ketones ; Montmorillonite ; Reagents ; Zirconium dioxide</subject><ispartof>RSC advances, 2024-10, Vol.14 (43), p.31675-31682</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2024</rights><rights>This journal is © The Royal Society of Chemistry 2024 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c318t-bc74c6436ababbec1eceec69968f9cf7a7eedfe98025ee6de75a5791e4fd00d23</cites><orcidid>0000-0002-4096-2293 ; 0000-0002-5204-772X ; 0000-0003-4844-8317</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457000/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC11457000/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39376529$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vergara-Arenas, Blanca I</creatorcontrib><creatorcontrib>García-Ríos, Eréndira</creatorcontrib><creatorcontrib>Gaviño, Rubén</creatorcontrib><creatorcontrib>Cárdenas, Jorge</creatorcontrib><creatorcontrib>Martinez-Garcia, Alfredo</creatorcontrib><creatorcontrib>Juarez-Arellano, Erick A</creatorcontrib><creatorcontrib>López-Torres, Adolfo</creatorcontrib><creatorcontrib>Morales-Serna, José A</creatorcontrib><title>Solid acids as cocatalysts in the chelation-assisted hydroacylation of alkenes and alkynes</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>The use of homogeneous Brønsted acid cocatalysts (such as benzoic acid) in hydroacylation reactions
via
imine intermediates has been extensively studied. However, the use of heterogeneous cocatalysts has been limited to montmorillonite K10. Thus, we can use other solid acids to increase the efficiency of the reaction. In this study, we describe the effects of sulfated zirconia, Al-MCM-41 or superacid modified montmorillonite on the hydroacylation of alkenes and alkynes with aldehydes
via
imine intermediates and in the presence of the Wilkinson complex. Furthermore, we addressed the dual role of montmorillonite, a redox reagent in the presence of TEMPO and an acid solid, allowing the direct use of benzyl alcohols as substrates to generate saturated or α,β-unsaturated ketones.
Hydroacylation of alkenes and alkynes in the presence of solid acids.</description><subject>Aldehydes</subject><subject>Alkenes</subject><subject>Alkynes</subject><subject>Benzoic acid</subject><subject>Benzyl alcohol</subject><subject>Chelation</subject><subject>Chemistry</subject><subject>Ketones</subject><subject>Montmorillonite</subject><subject>Reagents</subject><subject>Zirconium dioxide</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkUtr3DAUhUVJaYZkNt03CLIJASeSH7K1CiHNiw4U-th0I66l64xmPFYieQr-95Ez02kSbXTQ_Tjco0PIZ87OOMvkuck9sKKUfPmBTFKWiyRlQu690vtkGsKCxSMKngr-iexnMitFkcoJ-fPTtdZQ0NYECoFqp6GHdgh9oLaj_RypnmMLvXVdAiHY0KOh88F4B3rYvFPXUGiX2GG06Myoh6gPyccG2oDT7X1Aft9c_7q6S2bfb--vLmeJznjVJ7Uucy3yTEANdY2ao0bUQkpRNVI3JZSIpkFZsbRAFAbLAsa8mDeGMZNmB-Ri4_u4rldoNHa9h1Y9ersCPygHVr2ddHauHtxfxXlelPFbosPJ1sG7pzWGXq1s0Ni20KFbB5VFkhe8kiN6_A5duLXvYr6RKlnMkVaROt1Q2rsQPDa7bThTY23qa_7j8qW2bxE-er3_Dv1XUgS-bAAf9G76v_fsGTpgnxQ</recordid><startdate>20241001</startdate><enddate>20241001</enddate><creator>Vergara-Arenas, Blanca I</creator><creator>García-Ríos, Eréndira</creator><creator>Gaviño, Rubén</creator><creator>Cárdenas, Jorge</creator><creator>Martinez-Garcia, Alfredo</creator><creator>Juarez-Arellano, Erick A</creator><creator>López-Torres, Adolfo</creator><creator>Morales-Serna, José A</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-4096-2293</orcidid><orcidid>https://orcid.org/0000-0002-5204-772X</orcidid><orcidid>https://orcid.org/0000-0003-4844-8317</orcidid></search><sort><creationdate>20241001</creationdate><title>Solid acids as cocatalysts in the chelation-assisted hydroacylation of alkenes and alkynes</title><author>Vergara-Arenas, Blanca I ; García-Ríos, Eréndira ; Gaviño, Rubén ; Cárdenas, Jorge ; Martinez-Garcia, Alfredo ; Juarez-Arellano, Erick A ; López-Torres, Adolfo ; Morales-Serna, José A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c318t-bc74c6436ababbec1eceec69968f9cf7a7eedfe98025ee6de75a5791e4fd00d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Aldehydes</topic><topic>Alkenes</topic><topic>Alkynes</topic><topic>Benzoic acid</topic><topic>Benzyl alcohol</topic><topic>Chelation</topic><topic>Chemistry</topic><topic>Ketones</topic><topic>Montmorillonite</topic><topic>Reagents</topic><topic>Zirconium dioxide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vergara-Arenas, Blanca I</creatorcontrib><creatorcontrib>García-Ríos, Eréndira</creatorcontrib><creatorcontrib>Gaviño, Rubén</creatorcontrib><creatorcontrib>Cárdenas, Jorge</creatorcontrib><creatorcontrib>Martinez-Garcia, Alfredo</creatorcontrib><creatorcontrib>Juarez-Arellano, Erick A</creatorcontrib><creatorcontrib>López-Torres, Adolfo</creatorcontrib><creatorcontrib>Morales-Serna, José A</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vergara-Arenas, Blanca I</au><au>García-Ríos, Eréndira</au><au>Gaviño, Rubén</au><au>Cárdenas, Jorge</au><au>Martinez-Garcia, Alfredo</au><au>Juarez-Arellano, Erick A</au><au>López-Torres, Adolfo</au><au>Morales-Serna, José A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solid acids as cocatalysts in the chelation-assisted hydroacylation of alkenes and alkynes</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2024-10-01</date><risdate>2024</risdate><volume>14</volume><issue>43</issue><spage>31675</spage><epage>31682</epage><pages>31675-31682</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The use of homogeneous Brønsted acid cocatalysts (such as benzoic acid) in hydroacylation reactions
via
imine intermediates has been extensively studied. However, the use of heterogeneous cocatalysts has been limited to montmorillonite K10. Thus, we can use other solid acids to increase the efficiency of the reaction. In this study, we describe the effects of sulfated zirconia, Al-MCM-41 or superacid modified montmorillonite on the hydroacylation of alkenes and alkynes with aldehydes
via
imine intermediates and in the presence of the Wilkinson complex. Furthermore, we addressed the dual role of montmorillonite, a redox reagent in the presence of TEMPO and an acid solid, allowing the direct use of benzyl alcohols as substrates to generate saturated or α,β-unsaturated ketones.
Hydroacylation of alkenes and alkynes in the presence of solid acids.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>39376529</pmid><doi>10.1039/d4ra05791k</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-4096-2293</orcidid><orcidid>https://orcid.org/0000-0002-5204-772X</orcidid><orcidid>https://orcid.org/0000-0003-4844-8317</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; PubMed Central; EZB Electronic Journals Library; PubMed Central Open Access |
| subjects | Aldehydes Alkenes Alkynes Benzoic acid Benzyl alcohol Chelation Chemistry Ketones Montmorillonite Reagents Zirconium dioxide |
| title | Solid acids as cocatalysts in the chelation-assisted hydroacylation of alkenes and alkynes |
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