Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o -nitroaryl ureas
A simple and facile strategy to construct o -nitroaryl urea employing carbodiimides and ceric ammonium nitrate (CAN) has been developed. This protocol achieves the installation of two functional groups in one step with high functional group compatibility. Control experiments show that the reaction m...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2021-10, Vol.8 (20), p.5771-5776 |
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| container_issue | 20 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Wang, Shilong Xie, Xiangqi Zhao, Xingchen Liu, Jixin Zhao, Ziling Chen, Jinchun Li, Jiazhu Sun, Kai Zhang, Zhen |
| description | A simple and facile strategy to construct
o
-nitroaryl urea employing carbodiimides and ceric ammonium nitrate (CAN) has been developed. This protocol achieves the installation of two functional groups in one step with high functional group compatibility. Control experiments show that the reaction mechanism involves an intriguingly concerted nitration/ureation process enabled by CAN, and is distinctive from conventional electrophilic nitrification. The oxygen atom of urea probably originates from the nitrate ions provided by CAN. The late-stage derivatization and gram-scale synthesis reveal the promising utility of this methodology. |
| doi_str_mv | 10.1039/D1QO00943E |
| format | Article |
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o
-nitroaryl urea employing carbodiimides and ceric ammonium nitrate (CAN) has been developed. This protocol achieves the installation of two functional groups in one step with high functional group compatibility. Control experiments show that the reaction mechanism involves an intriguingly concerted nitration/ureation process enabled by CAN, and is distinctive from conventional electrophilic nitrification. The oxygen atom of urea probably originates from the nitrate ions provided by CAN. The late-stage derivatization and gram-scale synthesis reveal the promising utility of this methodology.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D1QO00943E</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Ammonium ; Ammonium nitrate ; Carbodiimides ; Cerium ammonium nitrate ; Controller area network ; Functional groups ; Nitrates ; Nitration ; Nitrification ; Organic chemistry ; Reaction mechanisms ; Urea ; Ureas</subject><ispartof>Organic Chemistry Frontiers, 2021-10, Vol.8 (20), p.5771-5776</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-d11bacc73e1b9180b9623e7f48df5194cb871ea648358ab04554c15806ae3c5f3</citedby><cites>FETCH-LOGICAL-c259t-d11bacc73e1b9180b9623e7f48df5194cb871ea648358ab04554c15806ae3c5f3</cites><orcidid>0000-0002-0041-6044 ; 0000-0003-4974-0598 ; 0000-0001-5550-2831</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Wang, Shilong</creatorcontrib><creatorcontrib>Xie, Xiangqi</creatorcontrib><creatorcontrib>Zhao, Xingchen</creatorcontrib><creatorcontrib>Liu, Jixin</creatorcontrib><creatorcontrib>Zhao, Ziling</creatorcontrib><creatorcontrib>Chen, Jinchun</creatorcontrib><creatorcontrib>Li, Jiazhu</creatorcontrib><creatorcontrib>Sun, Kai</creatorcontrib><creatorcontrib>Zhang, Zhen</creatorcontrib><title>Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o -nitroaryl ureas</title><title>Organic Chemistry Frontiers</title><description>A simple and facile strategy to construct
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-nitroaryl urea employing carbodiimides and ceric ammonium nitrate (CAN) has been developed. This protocol achieves the installation of two functional groups in one step with high functional group compatibility. Control experiments show that the reaction mechanism involves an intriguingly concerted nitration/ureation process enabled by CAN, and is distinctive from conventional electrophilic nitrification. The oxygen atom of urea probably originates from the nitrate ions provided by CAN. The late-stage derivatization and gram-scale synthesis reveal the promising utility of this methodology.</description><subject>Ammonium</subject><subject>Ammonium nitrate</subject><subject>Carbodiimides</subject><subject>Cerium ammonium nitrate</subject><subject>Controller area network</subject><subject>Functional groups</subject><subject>Nitrates</subject><subject>Nitration</subject><subject>Nitrification</subject><subject>Organic chemistry</subject><subject>Reaction mechanisms</subject><subject>Urea</subject><subject>Ureas</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpNkN1LwzAUxYMoOOZe_AsCvqhQl882eRx1fsBwCPpc0vQWM9ZmJunD_OvtnKBP9wf3nHsPB6FLSu4o4Xp-T1_XhGjBlydowohkmaBMn_7jczSLcUMIoUzmRBYTFEsIzmLTdb53Q4d7l4JJgK_LxcsNht7UW2iw9b2FkEY67p3v50OAH8C-xdaE2jfOda6BiJPHcd-nD4juC7DH2cHkTdhv8cEUL9BZa7YRZr9zit4flm_lU7ZaPz6Xi1VmmdQpayitjbUFB1prqkitc8ahaIVqWkm1sLUqKJhcKC6VqYmQUlgqFckNcCtbPkVXx7u74D8HiKna-CH048uKjTKlCsXZqLo9qmzwMQZoq11w3Zi2oqQ69Fr99cq_AZM1axI</recordid><startdate>20211012</startdate><enddate>20211012</enddate><creator>Wang, Shilong</creator><creator>Xie, Xiangqi</creator><creator>Zhao, Xingchen</creator><creator>Liu, Jixin</creator><creator>Zhao, Ziling</creator><creator>Chen, Jinchun</creator><creator>Li, Jiazhu</creator><creator>Sun, Kai</creator><creator>Zhang, Zhen</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-0041-6044</orcidid><orcidid>https://orcid.org/0000-0003-4974-0598</orcidid><orcidid>https://orcid.org/0000-0001-5550-2831</orcidid></search><sort><creationdate>20211012</creationdate><title>Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o -nitroaryl ureas</title><author>Wang, Shilong ; Xie, Xiangqi ; Zhao, Xingchen ; Liu, Jixin ; Zhao, Ziling ; Chen, Jinchun ; Li, Jiazhu ; Sun, Kai ; Zhang, Zhen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-d11bacc73e1b9180b9623e7f48df5194cb871ea648358ab04554c15806ae3c5f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Ammonium</topic><topic>Ammonium nitrate</topic><topic>Carbodiimides</topic><topic>Cerium ammonium nitrate</topic><topic>Controller area network</topic><topic>Functional groups</topic><topic>Nitrates</topic><topic>Nitration</topic><topic>Nitrification</topic><topic>Organic chemistry</topic><topic>Reaction mechanisms</topic><topic>Urea</topic><topic>Ureas</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Shilong</creatorcontrib><creatorcontrib>Xie, Xiangqi</creatorcontrib><creatorcontrib>Zhao, Xingchen</creatorcontrib><creatorcontrib>Liu, Jixin</creatorcontrib><creatorcontrib>Zhao, Ziling</creatorcontrib><creatorcontrib>Chen, Jinchun</creatorcontrib><creatorcontrib>Li, Jiazhu</creatorcontrib><creatorcontrib>Sun, Kai</creatorcontrib><creatorcontrib>Zhang, Zhen</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Shilong</au><au>Xie, Xiangqi</au><au>Zhao, Xingchen</au><au>Liu, Jixin</au><au>Zhao, Ziling</au><au>Chen, Jinchun</au><au>Li, Jiazhu</au><au>Sun, Kai</au><au>Zhang, Zhen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o -nitroaryl ureas</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2021-10-12</date><risdate>2021</risdate><volume>8</volume><issue>20</issue><spage>5771</spage><epage>5776</epage><pages>5771-5776</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>A simple and facile strategy to construct
o
-nitroaryl urea employing carbodiimides and ceric ammonium nitrate (CAN) has been developed. This protocol achieves the installation of two functional groups in one step with high functional group compatibility. Control experiments show that the reaction mechanism involves an intriguingly concerted nitration/ureation process enabled by CAN, and is distinctive from conventional electrophilic nitrification. The oxygen atom of urea probably originates from the nitrate ions provided by CAN. The late-stage derivatization and gram-scale synthesis reveal the promising utility of this methodology.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1QO00943E</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-0041-6044</orcidid><orcidid>https://orcid.org/0000-0003-4974-0598</orcidid><orcidid>https://orcid.org/0000-0001-5550-2831</orcidid></addata></record> |
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| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2021-10, Vol.8 (20), p.5771-5776 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Ammonium Ammonium nitrate Carbodiimides Cerium ammonium nitrate Controller area network Functional groups Nitrates Nitration Nitrification Organic chemistry Reaction mechanisms Urea Ureas |
| title | Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o -nitroaryl ureas |
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