Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu( i ) complexes under visible light
Herein, we report a substituent-controlled synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu( i ) complexes under visible-light irradiation. The in situ generated α-stilbene radical Cu( ii )-complex was a...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2022-11, Vol.24 (22), p.8685-8690 |
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| container_issue | 22 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Neerathilingam, Nalladhambi Prasanth, Kesavan Anandhan, Ramasamy |
| description | Herein, we report a substituent-controlled synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids
via
α-stilbene radicals obtained from heteroleptic Cu(
i
) complexes under visible-light irradiation. The
in situ
generated α-stilbene radical Cu(
ii
)-complex was achieved by photoinduced C
sp
–C
sp
2
coupling of copper(
i
) acetylides and aryl radicals catalysed by heteroleptic Cu(
i
) complexes. This photochemical approach offered high atom economy with a low
E
-factor and functional group tolerance under mild reaction conditions. Mechanistic insights clearly show that the reaction proceeded
via
copper(
i
) acetylides and the phenyl radical intermediate pathway. |
| doi_str_mv | 10.1039/D2GC03011J |
| format | Article |
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via
α-stilbene radicals obtained from heteroleptic Cu(
i
) complexes under visible-light irradiation. The
in situ
generated α-stilbene radical Cu(
ii
)-complex was achieved by photoinduced C
sp
–C
sp
2
coupling of copper(
i
) acetylides and aryl radicals catalysed by heteroleptic Cu(
i
) complexes. This photochemical approach offered high atom economy with a low
E
-factor and functional group tolerance under mild reaction conditions. Mechanistic insights clearly show that the reaction proceeded
via
copper(
i
) acetylides and the phenyl radical intermediate pathway.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/D2GC03011J</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alkynes ; Atom economy ; Copper ; Diketones ; Functional groups ; Green chemistry ; Irradiation ; Light irradiation ; Photochemicals ; Radicals ; Stilbene ; Synthesis</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2022-11, Vol.24 (22), p.8685-8690</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c189t-6897fd58fd4630a5343d50d3d1f7903a6b7188fdf68c5b7a98b46ae57bd54763</citedby><cites>FETCH-LOGICAL-c189t-6897fd58fd4630a5343d50d3d1f7903a6b7188fdf68c5b7a98b46ae57bd54763</cites><orcidid>0000-0001-7269-8776</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Neerathilingam, Nalladhambi</creatorcontrib><creatorcontrib>Prasanth, Kesavan</creatorcontrib><creatorcontrib>Anandhan, Ramasamy</creatorcontrib><title>Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu( i ) complexes under visible light</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>Herein, we report a substituent-controlled synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids
via
α-stilbene radicals obtained from heteroleptic Cu(
i
) complexes under visible-light irradiation. The
in situ
generated α-stilbene radical Cu(
ii
)-complex was achieved by photoinduced C
sp
–C
sp
2
coupling of copper(
i
) acetylides and aryl radicals catalysed by heteroleptic Cu(
i
) complexes. This photochemical approach offered high atom economy with a low
E
-factor and functional group tolerance under mild reaction conditions. Mechanistic insights clearly show that the reaction proceeded
via
copper(
i
) acetylides and the phenyl radical intermediate pathway.</description><subject>Alkynes</subject><subject>Atom economy</subject><subject>Copper</subject><subject>Diketones</subject><subject>Functional groups</subject><subject>Green chemistry</subject><subject>Irradiation</subject><subject>Light irradiation</subject><subject>Photochemicals</subject><subject>Radicals</subject><subject>Stilbene</subject><subject>Synthesis</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNkU1OwzAQhSMEEr8bTmCJDSACdpzEyRIVKCAkFrCP_DOhLq5dbKeix-IiLDkPLiBgNdbzm29Gb7Jsn-BTgml7dlGMR5hiQm7Xsi1S1jRvC4bXf991sZlthzDFycLqciv7eBhEiDoOYGMunY3eGQMKBTAgo14ACksbJxB0QK5H5KTIlX6G6CwExK1C2kbwlhvEzfNyJfbezVDSZvq_urJyvzTCeWe1RFxqFdBCc_T-lqcFjAALyHOlJTdplIhc27THF20CiecMzGPqHA2HSKMjJN1sbuA1sQerwCdW0MIAMvppEnezjT5xYO-n7mSPV5ePo-v87n58Mzq_yyVp2pjXTct6VTW9SvFgXtGSqgorqkjPWkx5LRhp0m9fN7ISjLeNKGsOFROqKllNd7KDb-zcu5cBQuymblilEbqC0aqpSFG2yXX87ZLeheCh7-Zez1IaHcHd6mzd39noJwQgkCo</recordid><startdate>20221114</startdate><enddate>20221114</enddate><creator>Neerathilingam, Nalladhambi</creator><creator>Prasanth, Kesavan</creator><creator>Anandhan, Ramasamy</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/0000-0001-7269-8776</orcidid></search><sort><creationdate>20221114</creationdate><title>Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu( i ) complexes under visible light</title><author>Neerathilingam, Nalladhambi ; Prasanth, Kesavan ; Anandhan, Ramasamy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c189t-6897fd58fd4630a5343d50d3d1f7903a6b7188fdf68c5b7a98b46ae57bd54763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkynes</topic><topic>Atom economy</topic><topic>Copper</topic><topic>Diketones</topic><topic>Functional groups</topic><topic>Green chemistry</topic><topic>Irradiation</topic><topic>Light irradiation</topic><topic>Photochemicals</topic><topic>Radicals</topic><topic>Stilbene</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Neerathilingam, Nalladhambi</creatorcontrib><creatorcontrib>Prasanth, Kesavan</creatorcontrib><creatorcontrib>Anandhan, Ramasamy</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>Neerathilingam, Nalladhambi</au><au>Prasanth, Kesavan</au><au>Anandhan, Ramasamy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu( i ) complexes under visible light</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2022-11-14</date><risdate>2022</risdate><volume>24</volume><issue>22</issue><spage>8685</spage><epage>8690</epage><pages>8685-8690</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>Herein, we report a substituent-controlled synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids
via
α-stilbene radicals obtained from heteroleptic Cu(
i
) complexes under visible-light irradiation. The
in situ
generated α-stilbene radical Cu(
ii
)-complex was achieved by photoinduced C
sp
–C
sp
2
coupling of copper(
i
) acetylides and aryl radicals catalysed by heteroleptic Cu(
i
) complexes. This photochemical approach offered high atom economy with a low
E
-factor and functional group tolerance under mild reaction conditions. Mechanistic insights clearly show that the reaction proceeded
via
copper(
i
) acetylides and the phenyl radical intermediate pathway.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D2GC03011J</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-7269-8776</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2022-11, Vol.24 (22), p.8685-8690 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_proquest_journals_2735851249 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkynes Atom economy Copper Diketones Functional groups Green chemistry Irradiation Light irradiation Photochemicals Radicals Stilbene Synthesis |
| title | Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu( i ) complexes under visible light |
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