Cu/photoredox-catalyzed decarboxylative radical C(sp3)-C(sp3) cross-coupling reactions
A radical decarboxylative C(sp 3 )-C(sp 3 ) cross-coupling of NHPI esters and cyclopropanols was developed by combining photocatalysis and copper catalysis, which presents the efficient access to β-benzyl ketones in excellent yields. Terpyridin-4′-one used as the ligand is vital for the reaction, wh...
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| Veröffentlicht in: | Science China. Chemistry 2023-10, Vol.66 (10), p.2858-2862 |
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| container_issue | 10 |
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| container_title | Science China. Chemistry |
| container_volume | 66 |
| creator | Jiang, Chao Chen, Pinhong Liu, Guosheng |
| description | A radical decarboxylative C(sp
3
)-C(sp
3
) cross-coupling of NHPI esters and cyclopropanols was developed by combining photocatalysis and copper catalysis, which presents the efficient access to β-benzyl ketones in excellent yields. Terpyridin-4′-one used as the ligand is vital for the reaction, which could facilitate the capture of benzylic radicals by alkyl-copper species generated from copper-catalyzed ring-opening of cyclopropanols. The reaction exhibited broad substrate scope and wide functional group compatibility, providing an alternative approach for C(sp
3
)-C(sp
3
) bond formation. |
| doi_str_mv | 10.1007/s11426-023-1762-6 |
| format | Article |
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3
)-C(sp
3
) cross-coupling of NHPI esters and cyclopropanols was developed by combining photocatalysis and copper catalysis, which presents the efficient access to β-benzyl ketones in excellent yields. Terpyridin-4′-one used as the ligand is vital for the reaction, which could facilitate the capture of benzylic radicals by alkyl-copper species generated from copper-catalyzed ring-opening of cyclopropanols. The reaction exhibited broad substrate scope and wide functional group compatibility, providing an alternative approach for C(sp
3
)-C(sp
3
) bond formation.</description><identifier>ISSN: 1674-7291</identifier><identifier>EISSN: 1869-1870</identifier><identifier>DOI: 10.1007/s11426-023-1762-6</identifier><language>eng</language><publisher>Beijing: Science China Press</publisher><subject>Acids ; Carbon ; Catalysis ; Chemical reactions ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Copper ; Cross coupling ; Esters ; Functional groups ; Ketones ; Ligands ; Light emitting diodes ; Photocatalysis ; Photoredox catalysis ; Reagents ; Ring opening ; Substrates</subject><ispartof>Science China. Chemistry, 2023-10, Vol.66 (10), p.2858-2862</ispartof><rights>Science China Press 2023</rights><rights>Science China Press 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-104f9b47cfb3b4ef505c1892ca8bab0348b529bb9bb3b8daa0668f1e567cf4f23</citedby><cites>FETCH-LOGICAL-c316t-104f9b47cfb3b4ef505c1892ca8bab0348b529bb9bb3b8daa0668f1e567cf4f23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11426-023-1762-6$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2918623081?pq-origsite=primo$$EHTML$$P50$$Gproquest$$H</linktohtml><link.rule.ids>314,780,784,21386,21387,21388,21389,23254,27922,27923,33528,33701,33742,34003,34312,41486,42555,43657,43785,43803,43951,44065,51317,64383,64387,72239</link.rule.ids></links><search><creatorcontrib>Jiang, Chao</creatorcontrib><creatorcontrib>Chen, Pinhong</creatorcontrib><creatorcontrib>Liu, Guosheng</creatorcontrib><title>Cu/photoredox-catalyzed decarboxylative radical C(sp3)-C(sp3) cross-coupling reactions</title><title>Science China. Chemistry</title><addtitle>Sci. China Chem</addtitle><description>A radical decarboxylative C(sp
3
)-C(sp
3
) cross-coupling of NHPI esters and cyclopropanols was developed by combining photocatalysis and copper catalysis, which presents the efficient access to β-benzyl ketones in excellent yields. Terpyridin-4′-one used as the ligand is vital for the reaction, which could facilitate the capture of benzylic radicals by alkyl-copper species generated from copper-catalyzed ring-opening of cyclopropanols. The reaction exhibited broad substrate scope and wide functional group compatibility, providing an alternative approach for C(sp
3
)-C(sp
3
) bond formation.</description><subject>Acids</subject><subject>Carbon</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Copper</subject><subject>Cross coupling</subject><subject>Esters</subject><subject>Functional groups</subject><subject>Ketones</subject><subject>Ligands</subject><subject>Light emitting diodes</subject><subject>Photocatalysis</subject><subject>Photoredox catalysis</subject><subject>Reagents</subject><subject>Ring opening</subject><subject>Substrates</subject><issn>1674-7291</issn><issn>1869-1870</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNp1UE1LxDAQDaLgsu4P8Fbwooe4maRN06MUv2DBi3oNSZquXWpTk1a2_nqzVvDkMPDm8N6bmYfQOZBrICRfB4CUckwow5BzivkRWoDgBQaRk-M48zzFOS3gFK1C2JFYjBGaZwv0Wo7r_s0NztvK7bFRg2qnL1sllTXKa7efWjU0nzbxqmqMapPyMvTsCs-QGO9CwMaNfdt028RbZYbGdeEMndSqDXb1i0v0cnf7XD7gzdP9Y3mzwYYBHzCQtC50mptaM53aOiOZAVFQo4RWmrBU6IwWWsdmWlRKEc5FDTbjUZLWlC3Rxezbe_cx2jDInRt9F1fK-K7glBEBkQUz6-dcb2vZ--Zd-UkCkYcE5ZygjAnKQ4KSRw2dNSFyu631f87_i74BKydzhA</recordid><startdate>20231001</startdate><enddate>20231001</enddate><creator>Jiang, Chao</creator><creator>Chen, Pinhong</creator><creator>Liu, Guosheng</creator><general>Science China Press</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7XB</scope><scope>88I</scope><scope>8FE</scope><scope>8FG</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>M2P</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>20231001</creationdate><title>Cu/photoredox-catalyzed decarboxylative radical C(sp3)-C(sp3) cross-coupling reactions</title><author>Jiang, Chao ; Chen, Pinhong ; Liu, Guosheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-104f9b47cfb3b4ef505c1892ca8bab0348b529bb9bb3b8daa0668f1e567cf4f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acids</topic><topic>Carbon</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Copper</topic><topic>Cross coupling</topic><topic>Esters</topic><topic>Functional groups</topic><topic>Ketones</topic><topic>Ligands</topic><topic>Light emitting diodes</topic><topic>Photocatalysis</topic><topic>Photoredox catalysis</topic><topic>Reagents</topic><topic>Ring opening</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Chao</creatorcontrib><creatorcontrib>Chen, Pinhong</creatorcontrib><creatorcontrib>Liu, Guosheng</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><jtitle>Science China. Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jiang, Chao</au><au>Chen, Pinhong</au><au>Liu, Guosheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cu/photoredox-catalyzed decarboxylative radical C(sp3)-C(sp3) cross-coupling reactions</atitle><jtitle>Science China. Chemistry</jtitle><stitle>Sci. China Chem</stitle><date>2023-10-01</date><risdate>2023</risdate><volume>66</volume><issue>10</issue><spage>2858</spage><epage>2862</epage><pages>2858-2862</pages><issn>1674-7291</issn><eissn>1869-1870</eissn><abstract>A radical decarboxylative C(sp
3
)-C(sp
3
) cross-coupling of NHPI esters and cyclopropanols was developed by combining photocatalysis and copper catalysis, which presents the efficient access to β-benzyl ketones in excellent yields. Terpyridin-4′-one used as the ligand is vital for the reaction, which could facilitate the capture of benzylic radicals by alkyl-copper species generated from copper-catalyzed ring-opening of cyclopropanols. The reaction exhibited broad substrate scope and wide functional group compatibility, providing an alternative approach for C(sp
3
)-C(sp
3
) bond formation.</abstract><cop>Beijing</cop><pub>Science China Press</pub><doi>10.1007/s11426-023-1762-6</doi><tpages>5</tpages></addata></record> |
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| issn | 1674-7291 1869-1870 |
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| subjects | Acids Carbon Catalysis Chemical reactions Chemistry Chemistry and Materials Science Chemistry/Food Science Copper Cross coupling Esters Functional groups Ketones Ligands Light emitting diodes Photocatalysis Photoredox catalysis Reagents Ring opening Substrates |
| title | Cu/photoredox-catalyzed decarboxylative radical C(sp3)-C(sp3) cross-coupling reactions |
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