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Iron-catalyzed ring-opening of cyclic carboxylic acids enabled by photoinduced ligand-to-metal charge transfer
A decarboxylative ring-opening protocol of cyclic tertiary carboxylic acids via iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) is described. This reaction enables the preparation of 1, n -dicarbonyl compounds through the homolytic C-C bond cleavage of unstrained carbocyclic and h...
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| Published in: | Green chemistry : an international journal and green chemistry resource : GC 2022-07, Vol.24 (14), p.5553-5558 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c281t-909430ad5565aa852e80ec5664814aecc9657a63ba5244b1972a5747589662883 |
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| cites | cdi_FETCH-LOGICAL-c281t-909430ad5565aa852e80ec5664814aecc9657a63ba5244b1972a5747589662883 |
| container_end_page | 5558 |
| container_issue | 14 |
| container_start_page | 5553 |
| container_title | Green chemistry : an international journal and green chemistry resource : GC |
| container_volume | 24 |
| creator | Tu, Jia-Lin Gao, Han Luo, Mengqi Zhao, Lulu Yang, Chao Guo, Lin Xia, Wujiong |
| description | A decarboxylative ring-opening protocol of cyclic tertiary carboxylic acids
via
iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) is described. This reaction enables the preparation of 1,
n
-dicarbonyl compounds through the homolytic C-C bond cleavage of unstrained carbocyclic and heterocyclic ring systems. This method exhibits a lot of synthetic advantages including mild conditions, simple operation, and convenience of amplification. Mechanistic studies support the generation of peroxy radical species
via
oxygen capture followed by radical fragmentation.
A decarboxylative ring-opening reaction of cyclic tertiary carboxylic acids
via
an iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) process is herein reported. |
| doi_str_mv | 10.1039/d2gc01738e |
| format | article |
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via
iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) is described. This reaction enables the preparation of 1,
n
-dicarbonyl compounds through the homolytic C-C bond cleavage of unstrained carbocyclic and heterocyclic ring systems. This method exhibits a lot of synthetic advantages including mild conditions, simple operation, and convenience of amplification. Mechanistic studies support the generation of peroxy radical species
via
oxygen capture followed by radical fragmentation.
A decarboxylative ring-opening reaction of cyclic tertiary carboxylic acids
via
an iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) process is herein reported.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/d2gc01738e</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Carbonyl compounds ; Carboxylic acids ; Charge transfer ; Covalent bonds ; Green chemistry ; Iron ; Ligands ; Peroxy radicals ; Ring opening</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2022-07, Vol.24 (14), p.5553-5558</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-909430ad5565aa852e80ec5664814aecc9657a63ba5244b1972a5747589662883</citedby><cites>FETCH-LOGICAL-c281t-909430ad5565aa852e80ec5664814aecc9657a63ba5244b1972a5747589662883</cites><orcidid>0000-0001-9396-9520 ; 0000-0003-0396-5935 ; 0000-0003-1103-0056</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Tu, Jia-Lin</creatorcontrib><creatorcontrib>Gao, Han</creatorcontrib><creatorcontrib>Luo, Mengqi</creatorcontrib><creatorcontrib>Zhao, Lulu</creatorcontrib><creatorcontrib>Yang, Chao</creatorcontrib><creatorcontrib>Guo, Lin</creatorcontrib><creatorcontrib>Xia, Wujiong</creatorcontrib><title>Iron-catalyzed ring-opening of cyclic carboxylic acids enabled by photoinduced ligand-to-metal charge transfer</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>A decarboxylative ring-opening protocol of cyclic tertiary carboxylic acids
via
iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) is described. This reaction enables the preparation of 1,
n
-dicarbonyl compounds through the homolytic C-C bond cleavage of unstrained carbocyclic and heterocyclic ring systems. This method exhibits a lot of synthetic advantages including mild conditions, simple operation, and convenience of amplification. Mechanistic studies support the generation of peroxy radical species
via
oxygen capture followed by radical fragmentation.
A decarboxylative ring-opening reaction of cyclic tertiary carboxylic acids
via
an iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) process is herein reported.</description><subject>Carbonyl compounds</subject><subject>Carboxylic acids</subject><subject>Charge transfer</subject><subject>Covalent bonds</subject><subject>Green chemistry</subject><subject>Iron</subject><subject>Ligands</subject><subject>Peroxy radicals</subject><subject>Ring opening</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpFkM9LwzAYhoMoOKcX70LBmxDN7yZHmXMKAy96Ll_TtOvokpl0YP3r7ZzM0_t-8PB-8CB0Tck9Jdw8VKyxhOZcuxM0oUJxbFhOTo9dsXN0kdKaEEpzJSbIv8bgsYUeuuHbVVlsfYPD1vkxs1BndrBdazMLsQxfw76CbauUOQ9lN_LlkG1XoQ-tr3Z2vLu2AV_hPuCNGzczu4LYuKyP4FPt4iU6q6FL7uovp-jjef4-e8HLt8Xr7HGJLdO0x4YYwQlUUioJoCVzmjgrlRKaCnDWGiVzULwEyYQoqckZyFzkUhulmNZ8im4Pu9sYPncu9cU67KIfXxZMGUoYF0qN1N2BsjGkFF1dbGO7gTgUlBR7n8UTW8x-fc5H-OYAx2SP3L9v_gN-DXHZ</recordid><startdate>20220718</startdate><enddate>20220718</enddate><creator>Tu, Jia-Lin</creator><creator>Gao, Han</creator><creator>Luo, Mengqi</creator><creator>Zhao, Lulu</creator><creator>Yang, Chao</creator><creator>Guo, Lin</creator><creator>Xia, Wujiong</creator><general>Royal Society of Chemistry</general><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><orcidid>https://orcid.org/0000-0001-9396-9520</orcidid><orcidid>https://orcid.org/0000-0003-0396-5935</orcidid><orcidid>https://orcid.org/0000-0003-1103-0056</orcidid></search><sort><creationdate>20220718</creationdate><title>Iron-catalyzed ring-opening of cyclic carboxylic acids enabled by photoinduced ligand-to-metal charge transfer</title><author>Tu, Jia-Lin ; Gao, Han ; Luo, Mengqi ; Zhao, Lulu ; Yang, Chao ; Guo, Lin ; Xia, Wujiong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-909430ad5565aa852e80ec5664814aecc9657a63ba5244b1972a5747589662883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Carbonyl compounds</topic><topic>Carboxylic acids</topic><topic>Charge transfer</topic><topic>Covalent bonds</topic><topic>Green chemistry</topic><topic>Iron</topic><topic>Ligands</topic><topic>Peroxy radicals</topic><topic>Ring opening</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tu, Jia-Lin</creatorcontrib><creatorcontrib>Gao, Han</creatorcontrib><creatorcontrib>Luo, Mengqi</creatorcontrib><creatorcontrib>Zhao, Lulu</creatorcontrib><creatorcontrib>Yang, Chao</creatorcontrib><creatorcontrib>Guo, Lin</creatorcontrib><creatorcontrib>Xia, Wujiong</creatorcontrib><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><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>Tu, Jia-Lin</au><au>Gao, Han</au><au>Luo, Mengqi</au><au>Zhao, Lulu</au><au>Yang, Chao</au><au>Guo, Lin</au><au>Xia, Wujiong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iron-catalyzed ring-opening of cyclic carboxylic acids enabled by photoinduced ligand-to-metal charge transfer</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2022-07-18</date><risdate>2022</risdate><volume>24</volume><issue>14</issue><spage>5553</spage><epage>5558</epage><pages>5553-5558</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>A decarboxylative ring-opening protocol of cyclic tertiary carboxylic acids
via
iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) is described. This reaction enables the preparation of 1,
n
-dicarbonyl compounds through the homolytic C-C bond cleavage of unstrained carbocyclic and heterocyclic ring systems. This method exhibits a lot of synthetic advantages including mild conditions, simple operation, and convenience of amplification. Mechanistic studies support the generation of peroxy radical species
via
oxygen capture followed by radical fragmentation.
A decarboxylative ring-opening reaction of cyclic tertiary carboxylic acids
via
an iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) process is herein reported.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2gc01738e</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-9396-9520</orcidid><orcidid>https://orcid.org/0000-0003-0396-5935</orcidid><orcidid>https://orcid.org/0000-0003-1103-0056</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2022-07, Vol.24 (14), p.5553-5558 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_rsc_primary_d2gc01738e |
| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Carbonyl compounds Carboxylic acids Charge transfer Covalent bonds Green chemistry Iron Ligands Peroxy radicals Ring opening |
| title | Iron-catalyzed ring-opening of cyclic carboxylic acids enabled by photoinduced ligand-to-metal charge transfer |
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