Cercosporin-bioinspired selective photooxidation reactions under mild conditions
The development of an efficient system for selective oxidation of organic compounds to generate more valuable compounds with molecular oxygen is a significant challenge in industrial chemistry. Bioinspired by the ability of naturally occurring perylenequinonoid pigments (PQPs) to generate reactive o...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2019, Vol.21 (22), p.673-681 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Li, Jia Bao, Wenhao Tang, Zhaocheng Guo, Baodang Zhang, Shiwei Liu, Haili Huang, Shuping Zhang, Yan Rao, Yijian |
| description | The development of an efficient system for selective oxidation of organic compounds to generate more valuable compounds with molecular oxygen is a significant challenge in industrial chemistry. Bioinspired by the ability of naturally occurring perylenequinonoid pigments (PQPs) to generate reactive oxygen species (ROS) upon photoirradiation, here we report that cercosporin, one of the perylenequinonoid pigments, can function as a cost-effective and environmentally friendly photocatalyst for a wide range of selective oxidations, including benzylic C-H bonds to carbonyls, amines to aldehydes, and sulfides to sulfoxides. All of the representative reactions proceeded smoothly with high efficiency under mild conditions. Owing to the use of inexpensive metal-free visible light-driven photocatalyst produced from microbial fermentation with cheap glucose as the starting material and the ease of handling, we expect that this developed method will be particularly attractive for many more applications in synthetic transformation.
Cercosporin was developed as a green and efficient organophotocatalyst for a wide range of selective oxidations with reactive oxygen species. |
| doi_str_mv | 10.1039/c9gc02270h |
| format | Article |
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Cercosporin was developed as a green and efficient organophotocatalyst for a wide range of selective oxidations with reactive oxygen species.</description><subject>Aldehydes</subject><subject>Amines</subject><subject>Carbonyl compounds</subject><subject>Carbonyls</subject><subject>Cercosporin</subject><subject>Fermentation</subject><subject>Green chemistry</subject><subject>Materials handling</subject><subject>Microorganisms</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Oxidation</subject><subject>Oxygen</subject><subject>Photocatalysts</subject><subject>Photooxidation</subject><subject>Pigments</subject><subject>Reactive oxygen species</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpFkE1Lw0AQhhdRsFYv3oWANyE6u5vux1GCtkJBD3oOyezWbkmzcTcR_fdNG6mneWd4eAceQq4p3FPg-gH1JwJjEtYnZEIzwVM9LKfHLNg5uYhxA0CpFNmEvOU2oI-tD65JK-ddE1sXrEmirS127tsm7dp33v84U3bON0mwJe5DTPrG2JBsXW0S9I1xh-slOVuVdbRXf3NKPp6f3vNFunydv-SPyxQ5VV1qmGI6q5QSpiqh1MiZmoHVQgAA8kxWVGSZ1Ci5kFQDDPxMoUFTMaoE5VNyO_a2wX_1NnbFxvehGV4WjFM-NEiuB-pupDD4GINdFW1w2zL8FhSKvbEi1_P8YGwxwDcjHCIeuX-jfAeRFWfL</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Li, Jia</creator><creator>Bao, Wenhao</creator><creator>Tang, Zhaocheng</creator><creator>Guo, Baodang</creator><creator>Zhang, Shiwei</creator><creator>Liu, Haili</creator><creator>Huang, Shuping</creator><creator>Zhang, Yan</creator><creator>Rao, Yijian</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/0000-0003-4815-1863</orcidid><orcidid>https://orcid.org/0000-0002-4941-8622</orcidid><orcidid>https://orcid.org/0000-0003-2481-0588</orcidid></search><sort><creationdate>2019</creationdate><title>Cercosporin-bioinspired selective photooxidation reactions under mild conditions</title><author>Li, Jia ; Bao, Wenhao ; Tang, Zhaocheng ; Guo, Baodang ; Zhang, Shiwei ; Liu, Haili ; Huang, Shuping ; Zhang, Yan ; Rao, Yijian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c318t-d28294b886dba0a9c32850e966000c347b164479c7367190028258cdcdb218613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aldehydes</topic><topic>Amines</topic><topic>Carbonyl compounds</topic><topic>Carbonyls</topic><topic>Cercosporin</topic><topic>Fermentation</topic><topic>Green chemistry</topic><topic>Materials handling</topic><topic>Microorganisms</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Oxidation</topic><topic>Oxygen</topic><topic>Photocatalysts</topic><topic>Photooxidation</topic><topic>Pigments</topic><topic>Reactive oxygen species</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jia</creatorcontrib><creatorcontrib>Bao, Wenhao</creatorcontrib><creatorcontrib>Tang, Zhaocheng</creatorcontrib><creatorcontrib>Guo, Baodang</creatorcontrib><creatorcontrib>Zhang, Shiwei</creatorcontrib><creatorcontrib>Liu, Haili</creatorcontrib><creatorcontrib>Huang, Shuping</creatorcontrib><creatorcontrib>Zhang, Yan</creatorcontrib><creatorcontrib>Rao, Yijian</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>Li, Jia</au><au>Bao, Wenhao</au><au>Tang, Zhaocheng</au><au>Guo, Baodang</au><au>Zhang, Shiwei</au><au>Liu, Haili</au><au>Huang, Shuping</au><au>Zhang, Yan</au><au>Rao, Yijian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cercosporin-bioinspired selective photooxidation reactions under mild conditions</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2019</date><risdate>2019</risdate><volume>21</volume><issue>22</issue><spage>673</spage><epage>681</epage><pages>673-681</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>The development of an efficient system for selective oxidation of organic compounds to generate more valuable compounds with molecular oxygen is a significant challenge in industrial chemistry. Bioinspired by the ability of naturally occurring perylenequinonoid pigments (PQPs) to generate reactive oxygen species (ROS) upon photoirradiation, here we report that cercosporin, one of the perylenequinonoid pigments, can function as a cost-effective and environmentally friendly photocatalyst for a wide range of selective oxidations, including benzylic C-H bonds to carbonyls, amines to aldehydes, and sulfides to sulfoxides. All of the representative reactions proceeded smoothly with high efficiency under mild conditions. Owing to the use of inexpensive metal-free visible light-driven photocatalyst produced from microbial fermentation with cheap glucose as the starting material and the ease of handling, we expect that this developed method will be particularly attractive for many more applications in synthetic transformation.
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| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2019, Vol.21 (22), p.673-681 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aldehydes Amines Carbonyl compounds Carbonyls Cercosporin Fermentation Green chemistry Materials handling Microorganisms Organic chemistry Organic compounds Oxidation Oxygen Photocatalysts Photooxidation Pigments Reactive oxygen species |
| title | Cercosporin-bioinspired selective photooxidation reactions under mild conditions |
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