A highly efficient and sustainable catalyst system for terminal epoxy-carboxylic acid ring opening reactions
The nucleophilic ring opening of epoxides by carboxylic acids is an indispensable transformation for materials science and coating technologies. Due to this industrial significance, improvements in operational energy consumption and catalyst sustainability are highly desirable for this transformatio...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2024-03, Vol.26 (6), p.3346-3355 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Ramspoth, Tizian-Frank Flapper, Jitte van den Berg, Keimpe J Feringa, Ben L Harutyunyan, Syuzanna R |
| description | The nucleophilic ring opening of epoxides by carboxylic acids is an indispensable transformation for materials science and coating technologies. Due to this industrial significance, improvements in operational energy consumption and catalyst sustainability are highly desirable for this transformation. Herein, an efficient, environmentally benign and non-toxic halide free cooperative catalyst system based on an iron(
iii
) benzoate complex and guanidinium carbonate is reported. The novel catalyst system shows improved activity over onium halide catalysts under neat conditions and in several solvents, including anisole and
n
BuOAc. Detailed mechanistic studies using FeCl
3
/DMAP as a catalyst revealed the importance of a carboxylate bridged cationic trinuclear μ
3
-oxo iron cluster and guanidinium carbonate or DMAP as a carboxylate reservoir due to its superior activity.
An efficient, green, non-toxic, halide-free catalyst system with iron(
iii
) benzoate and guanidinium carbonate facilitates the nucleophilic ring opening of terminal epoxides by carboxylic acids, key process for materials science and coatings. |
| doi_str_mv | 10.1039/d3gc04301k |
| format | Article |
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iii
) benzoate complex and guanidinium carbonate is reported. The novel catalyst system shows improved activity over onium halide catalysts under neat conditions and in several solvents, including anisole and
n
BuOAc. Detailed mechanistic studies using FeCl
3
/DMAP as a catalyst revealed the importance of a carboxylate bridged cationic trinuclear μ
3
-oxo iron cluster and guanidinium carbonate or DMAP as a carboxylate reservoir due to its superior activity.
An efficient, green, non-toxic, halide-free catalyst system with iron(
iii
) benzoate and guanidinium carbonate facilitates the nucleophilic ring opening of terminal epoxides by carboxylic acids, key process for materials science and coatings.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>EISSN: 1463-9262</identifier><identifier>DOI: 10.1039/d3gc04301k</identifier><identifier>PMID: 38505506</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Anisole ; Benzoates ; Benzoic acid ; Carboxylic acids ; Catalysts ; Chemistry ; Energy consumption ; Epoxides ; Ferric chloride ; Iron ; Ring opening</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2024-03, Vol.26 (6), p.3346-3355</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><citedby>FETCH-LOGICAL-c429t-3b6ef80c658e68db53d5c9944d7583ecf35711b358f5e3e2fdbffed0b12932de3</citedby><cites>FETCH-LOGICAL-c429t-3b6ef80c658e68db53d5c9944d7583ecf35711b358f5e3e2fdbffed0b12932de3</cites><orcidid>0000-0002-9980-3289 ; 0000-0003-0588-8435 ; 0000-0003-2411-1250 ; 0009-0008-2751-9677</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38505506$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ramspoth, Tizian-Frank</creatorcontrib><creatorcontrib>Flapper, Jitte</creatorcontrib><creatorcontrib>van den Berg, Keimpe J</creatorcontrib><creatorcontrib>Feringa, Ben L</creatorcontrib><creatorcontrib>Harutyunyan, Syuzanna R</creatorcontrib><title>A highly efficient and sustainable catalyst system for terminal epoxy-carboxylic acid ring opening reactions</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><addtitle>Green Chem</addtitle><description>The nucleophilic ring opening of epoxides by carboxylic acids is an indispensable transformation for materials science and coating technologies. Due to this industrial significance, improvements in operational energy consumption and catalyst sustainability are highly desirable for this transformation. Herein, an efficient, environmentally benign and non-toxic halide free cooperative catalyst system based on an iron(
iii
) benzoate complex and guanidinium carbonate is reported. The novel catalyst system shows improved activity over onium halide catalysts under neat conditions and in several solvents, including anisole and
n
BuOAc. Detailed mechanistic studies using FeCl
3
/DMAP as a catalyst revealed the importance of a carboxylate bridged cationic trinuclear μ
3
-oxo iron cluster and guanidinium carbonate or DMAP as a carboxylate reservoir due to its superior activity.
An efficient, green, non-toxic, halide-free catalyst system with iron(
iii
) benzoate and guanidinium carbonate facilitates the nucleophilic ring opening of terminal epoxides by carboxylic acids, key process for materials science and coatings.</description><subject>Anisole</subject><subject>Benzoates</subject><subject>Benzoic acid</subject><subject>Carboxylic acids</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Energy consumption</subject><subject>Epoxides</subject><subject>Ferric chloride</subject><subject>Iron</subject><subject>Ring opening</subject><issn>1463-9262</issn><issn>1463-9270</issn><issn>1463-9262</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkt1vFCEUxYmxsbX64ruGxBdjMpWPgWGeTLNqbdrEF30mDFx2qcywwoxx_3tZt64fLxyS88vJ5R4QekbJBSW8f-P42pKWE_r1ATqjreRNzzry8HiX7BQ9LuWOEEo72T5Cp1wJIgSRZyhe4k1Yb-IOg_fBBphmbCaHy1JmEyYzRMDWzCbuyoxLPWDEPmU8Qx6rHTFs049dY00eqsZgsbHB4RymNU5bmPaawdg5pKk8QSfexAJP7_Ucffnw_vPqY3P76ep6dXnb2Jb1c8MHCV4RK4UCqdwguBO279vWdUJxsJ6LjtKBC-UFcGDeDd6DIwNlPWcO-Dl6e8jdLsMIztZHZRP1NofR5J1OJuh_nSls9Dp915T0rSJK1YRX9wk5fVugzHoMxUKMZoK0FM36rq5YEtJV9OV_6F1acl3NnpKSsJYwWanXB8rmVEoGf5yGEr1vUb_jV6tfLd5U-MXf8x_R37VV4PkByMUe3T_fgP8EL0akSw</recordid><startdate>20240318</startdate><enddate>20240318</enddate><creator>Ramspoth, Tizian-Frank</creator><creator>Flapper, Jitte</creator><creator>van den Berg, Keimpe J</creator><creator>Feringa, Ben L</creator><creator>Harutyunyan, Syuzanna R</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>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-9980-3289</orcidid><orcidid>https://orcid.org/0000-0003-0588-8435</orcidid><orcidid>https://orcid.org/0000-0003-2411-1250</orcidid><orcidid>https://orcid.org/0009-0008-2751-9677</orcidid></search><sort><creationdate>20240318</creationdate><title>A highly efficient and sustainable catalyst system for terminal epoxy-carboxylic acid ring opening reactions</title><author>Ramspoth, Tizian-Frank ; Flapper, Jitte ; van den Berg, Keimpe J ; Feringa, Ben L ; Harutyunyan, Syuzanna R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-3b6ef80c658e68db53d5c9944d7583ecf35711b358f5e3e2fdbffed0b12932de3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Anisole</topic><topic>Benzoates</topic><topic>Benzoic acid</topic><topic>Carboxylic acids</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Energy consumption</topic><topic>Epoxides</topic><topic>Ferric chloride</topic><topic>Iron</topic><topic>Ring opening</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ramspoth, Tizian-Frank</creatorcontrib><creatorcontrib>Flapper, Jitte</creatorcontrib><creatorcontrib>van den Berg, Keimpe J</creatorcontrib><creatorcontrib>Feringa, Ben L</creatorcontrib><creatorcontrib>Harutyunyan, Syuzanna R</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ramspoth, Tizian-Frank</au><au>Flapper, Jitte</au><au>van den Berg, Keimpe J</au><au>Feringa, Ben L</au><au>Harutyunyan, Syuzanna R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A highly efficient and sustainable catalyst system for terminal epoxy-carboxylic acid ring opening reactions</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><addtitle>Green Chem</addtitle><date>2024-03-18</date><risdate>2024</risdate><volume>26</volume><issue>6</issue><spage>3346</spage><epage>3355</epage><pages>3346-3355</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><eissn>1463-9262</eissn><abstract>The nucleophilic ring opening of epoxides by carboxylic acids is an indispensable transformation for materials science and coating technologies. Due to this industrial significance, improvements in operational energy consumption and catalyst sustainability are highly desirable for this transformation. Herein, an efficient, environmentally benign and non-toxic halide free cooperative catalyst system based on an iron(
iii
) benzoate complex and guanidinium carbonate is reported. The novel catalyst system shows improved activity over onium halide catalysts under neat conditions and in several solvents, including anisole and
n
BuOAc. Detailed mechanistic studies using FeCl
3
/DMAP as a catalyst revealed the importance of a carboxylate bridged cationic trinuclear μ
3
-oxo iron cluster and guanidinium carbonate or DMAP as a carboxylate reservoir due to its superior activity.
An efficient, green, non-toxic, halide-free catalyst system with iron(
iii
) benzoate and guanidinium carbonate facilitates the nucleophilic ring opening of terminal epoxides by carboxylic acids, key process for materials science and coatings.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38505506</pmid><doi>10.1039/d3gc04301k</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-9980-3289</orcidid><orcidid>https://orcid.org/0000-0003-0588-8435</orcidid><orcidid>https://orcid.org/0000-0003-2411-1250</orcidid><orcidid>https://orcid.org/0009-0008-2751-9677</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2024-03, Vol.26 (6), p.3346-3355 |
| issn | 1463-9262 1463-9270 1463-9262 |
| language | eng |
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| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Anisole Benzoates Benzoic acid Carboxylic acids Catalysts Chemistry Energy consumption Epoxides Ferric chloride Iron Ring opening |
| title | A highly efficient and sustainable catalyst system for terminal epoxy-carboxylic acid ring opening reactions |
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