Photoinduced C–O bond cleavage for copper-catalyzed allenyl radical cyanation
The selective activation and transformation of C–O bonds under mild conditions is of great significance in synthetic chemistry because of the widespread existence of carbon–oxygen single bonds. In this work, allenyl radicals were generated by the photoinduced cleavage of carbon–oxygen bonds, and par...
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Veröffentlicht in: | Organic Chemistry Frontiers 2022-09, Vol.9 (19), p.5259-5263 |
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creator | Lu, Fu-Dong Shu, Zhen-Cao He, Gui-Feng Bai, Jun-Chuan Lu, Liang-Qiu Xiao, Wen-Jing |
description | The selective activation and transformation of C–O bonds under mild conditions is of great significance in synthetic chemistry because of the widespread existence of carbon–oxygen single bonds. In this work, allenyl radicals were generated by the photoinduced cleavage of carbon–oxygen bonds, and participated in the copper catalytic cycle, affording structurally diverse and highly significant allenyl nitriles. Both 1,3-disubstituted allenyl nitriles and trisubstituted allenyl nitriles could be assembled with moderate to good yields (24 examples, 65–95% yields) and high chemoselectivity. To prove the utility of this new methodology, an allene nitrile was converted into other valuable synthetic blocks including an allyl nitrile, alkyl nitrile and α-cyano cyclic ketone. |
doi_str_mv | 10.1039/D2QO00938B |
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In this work, allenyl radicals were generated by the photoinduced cleavage of carbon–oxygen bonds, and participated in the copper catalytic cycle, affording structurally diverse and highly significant allenyl nitriles. Both 1,3-disubstituted allenyl nitriles and trisubstituted allenyl nitriles could be assembled with moderate to good yields (24 examples, 65–95% yields) and high chemoselectivity. To prove the utility of this new methodology, an allene nitrile was converted into other valuable synthetic blocks including an allyl nitrile, alkyl nitrile and α-cyano cyclic ketone.</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/D2QO00938B</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Carbon ; Cleavage ; Copper ; Cyanides ; Ketones ; Nitriles ; Organic chemistry ; Oxygen</subject><ispartof>Organic Chemistry Frontiers, 2022-09, Vol.9 (19), p.5259-5263</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c211t-6652996e30846cd7497e203bb93a96259362df07ae0ac573606cfc644e01309b3</citedby><cites>FETCH-LOGICAL-c211t-6652996e30846cd7497e203bb93a96259362df07ae0ac573606cfc644e01309b3</cites><orcidid>0000-0002-9318-6021 ; 0000-0003-2177-4729</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>Lu, Fu-Dong</creatorcontrib><creatorcontrib>Shu, Zhen-Cao</creatorcontrib><creatorcontrib>He, Gui-Feng</creatorcontrib><creatorcontrib>Bai, Jun-Chuan</creatorcontrib><creatorcontrib>Lu, Liang-Qiu</creatorcontrib><creatorcontrib>Xiao, Wen-Jing</creatorcontrib><title>Photoinduced C–O bond cleavage for copper-catalyzed allenyl radical cyanation</title><title>Organic Chemistry Frontiers</title><description>The selective activation and transformation of C–O bonds under mild conditions is of great significance in synthetic chemistry because of the widespread existence of carbon–oxygen single bonds. In this work, allenyl radicals were generated by the photoinduced cleavage of carbon–oxygen bonds, and participated in the copper catalytic cycle, affording structurally diverse and highly significant allenyl nitriles. Both 1,3-disubstituted allenyl nitriles and trisubstituted allenyl nitriles could be assembled with moderate to good yields (24 examples, 65–95% yields) and high chemoselectivity. To prove the utility of this new methodology, an allene nitrile was converted into other valuable synthetic blocks including an allyl nitrile, alkyl nitrile and α-cyano cyclic ketone.</description><subject>Carbon</subject><subject>Cleavage</subject><subject>Copper</subject><subject>Cyanides</subject><subject>Ketones</subject><subject>Nitriles</subject><subject>Organic chemistry</subject><subject>Oxygen</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNkM1KxDAUhYMoOIyz8QkC7oTqzU2TTpY6_sJAFXRdbtNUO8Smph2hrnwH39AncWQEXZ2z-DgHPsYOBZwIkOb0Au9zACPn5ztsgqAwSQWa3X99n836fgUAApUGlU1YfvcchtC01dq6ii--Pj5zXoa24tY7eqMnx-sQuQ1d52JiaSA_vm9A8t61o-eRqsaS53akloYmtAdsrybfu9lvTtnj1eXD4iZZ5te3i7NlYlGIIdFaoTHaSZin2lZZajKHIMvSSDIalZEaqxoyckBWZVKDtrXVaepASDClnLKj7W4Xw-va9UOxCuvYbi4LzMRcIKQKN9TxlrIx9H10ddHF5oXiWAgofpwVf87kN3j3XYw</recordid><startdate>20220927</startdate><enddate>20220927</enddate><creator>Lu, Fu-Dong</creator><creator>Shu, Zhen-Cao</creator><creator>He, Gui-Feng</creator><creator>Bai, Jun-Chuan</creator><creator>Lu, Liang-Qiu</creator><creator>Xiao, Wen-Jing</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/0000-0002-9318-6021</orcidid><orcidid>https://orcid.org/0000-0003-2177-4729</orcidid></search><sort><creationdate>20220927</creationdate><title>Photoinduced C–O bond cleavage for copper-catalyzed allenyl radical cyanation</title><author>Lu, Fu-Dong ; Shu, Zhen-Cao ; He, Gui-Feng ; Bai, Jun-Chuan ; Lu, Liang-Qiu ; Xiao, Wen-Jing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c211t-6652996e30846cd7497e203bb93a96259362df07ae0ac573606cfc644e01309b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Carbon</topic><topic>Cleavage</topic><topic>Copper</topic><topic>Cyanides</topic><topic>Ketones</topic><topic>Nitriles</topic><topic>Organic chemistry</topic><topic>Oxygen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lu, Fu-Dong</creatorcontrib><creatorcontrib>Shu, Zhen-Cao</creatorcontrib><creatorcontrib>He, Gui-Feng</creatorcontrib><creatorcontrib>Bai, Jun-Chuan</creatorcontrib><creatorcontrib>Lu, Liang-Qiu</creatorcontrib><creatorcontrib>Xiao, Wen-Jing</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>Lu, Fu-Dong</au><au>Shu, Zhen-Cao</au><au>He, Gui-Feng</au><au>Bai, Jun-Chuan</au><au>Lu, Liang-Qiu</au><au>Xiao, Wen-Jing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photoinduced C–O bond cleavage for copper-catalyzed allenyl radical cyanation</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2022-09-27</date><risdate>2022</risdate><volume>9</volume><issue>19</issue><spage>5259</spage><epage>5263</epage><pages>5259-5263</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>The selective activation and transformation of C–O bonds under mild conditions is of great significance in synthetic chemistry because of the widespread existence of carbon–oxygen single bonds. In this work, allenyl radicals were generated by the photoinduced cleavage of carbon–oxygen bonds, and participated in the copper catalytic cycle, affording structurally diverse and highly significant allenyl nitriles. Both 1,3-disubstituted allenyl nitriles and trisubstituted allenyl nitriles could be assembled with moderate to good yields (24 examples, 65–95% yields) and high chemoselectivity. To prove the utility of this new methodology, an allene nitrile was converted into other valuable synthetic blocks including an allyl nitrile, alkyl nitrile and α-cyano cyclic ketone.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D2QO00938B</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-9318-6021</orcidid><orcidid>https://orcid.org/0000-0003-2177-4729</orcidid></addata></record> |
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subjects | Carbon Cleavage Copper Cyanides Ketones Nitriles Organic chemistry Oxygen |
title | Photoinduced C–O bond cleavage for copper-catalyzed allenyl radical cyanation |
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