Site-selective coupling of remote C(sp 3 )-H/ meta -C(sp 2 )-H bonds enabled by Ru/photoredox dual catalysis and mechanistic studies
Construction of C(sp )-C(sp ) bonds regioselective coupling of C(sp )-H/C(sp )-H bonds is challenging due to the low reactivity and regioselectivity of C-H bonds. Here, a novel photoinduced Ru/photocatalyst-cocatalyzed regioselective cross-dehydrogenative coupling of dual remote C-H bonds, including...
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| Veröffentlicht in: | Chemical science (Cambridge) 2022-05, Vol.13 (18), p.5382-5389 |
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| creator | Liu, Hong-Chao Kong, Xiangtao Gong, Xiao-Ping Li, Yuke Niu, Zhi-Jie Gou, Xue-Ya Li, Xue-Song Wang, Yu-Zhao Shi, Wei-Yu Huang, Yan-Chong Liu, Xue-Yuan Liang, Yong-Min |
| description | Construction of C(sp
)-C(sp
) bonds
regioselective coupling of C(sp
)-H/C(sp
)-H bonds is challenging due to the low reactivity and regioselectivity of C-H bonds. Here, a novel photoinduced Ru/photocatalyst-cocatalyzed regioselective cross-dehydrogenative coupling of dual remote C-H bonds, including inert γ-C(sp
)-H bonds in amides and
-C(sp
)-H bonds in arenes, to construct
-alkylated arenes has been accomplished. This metallaphotoredox-enabled site-selective coupling between remote inert C(sp
)-H bonds and
-C(sp
)-H bonds is characterized by its unique site-selectivity, redox-neutral conditions, broad substrate scope and wide use of late-stage functionalization of bioactive molecules. Moreover, this reaction represents a novel case of regioselective cross-dehydrogenative coupling of unactivated alkanes and arenes
a new catalytic process and provides a new strategy for
-functionalized arenes under mild reaction conditions. Density functional theory (DFT) calculations and control experiments explained the site-selectivity and the detailed mechanism of this reaction. |
| doi_str_mv | 10.1039/d2sc00764a |
| format | Article |
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)-C(sp
) bonds
regioselective coupling of C(sp
)-H/C(sp
)-H bonds is challenging due to the low reactivity and regioselectivity of C-H bonds. Here, a novel photoinduced Ru/photocatalyst-cocatalyzed regioselective cross-dehydrogenative coupling of dual remote C-H bonds, including inert γ-C(sp
)-H bonds in amides and
-C(sp
)-H bonds in arenes, to construct
-alkylated arenes has been accomplished. This metallaphotoredox-enabled site-selective coupling between remote inert C(sp
)-H bonds and
-C(sp
)-H bonds is characterized by its unique site-selectivity, redox-neutral conditions, broad substrate scope and wide use of late-stage functionalization of bioactive molecules. Moreover, this reaction represents a novel case of regioselective cross-dehydrogenative coupling of unactivated alkanes and arenes
a new catalytic process and provides a new strategy for
-functionalized arenes under mild reaction conditions. Density functional theory (DFT) calculations and control experiments explained the site-selectivity and the detailed mechanism of this reaction.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d2sc00764a</identifier><identifier>PMID: 35655562</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkanes ; Alkylation ; Amides ; Aromatic compounds ; Catalysis ; Chemistry ; Coupling (molecular) ; Dehydrogenation ; Density functional theory ; Regioselectivity ; Selectivity ; Substrates</subject><ispartof>Chemical science (Cambridge), 2022-05, Vol.13 (18), p.5382-5389</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2022</rights><rights>This journal is © The Royal Society of Chemistry 2022 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c336t-6092dc9e916fecc9df8f2c89db9a37d73c7275a4abfaf6a1b89c8d22e5f5f6003</citedby><cites>FETCH-LOGICAL-c336t-6092dc9e916fecc9df8f2c89db9a37d73c7275a4abfaf6a1b89c8d22e5f5f6003</cites><orcidid>0000-0001-8280-8211 ; 0000-0003-0162-5072 ; 0000-0002-8862-9924</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9093131/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9093131/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35655562$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Hong-Chao</creatorcontrib><creatorcontrib>Kong, Xiangtao</creatorcontrib><creatorcontrib>Gong, Xiao-Ping</creatorcontrib><creatorcontrib>Li, Yuke</creatorcontrib><creatorcontrib>Niu, Zhi-Jie</creatorcontrib><creatorcontrib>Gou, Xue-Ya</creatorcontrib><creatorcontrib>Li, Xue-Song</creatorcontrib><creatorcontrib>Wang, Yu-Zhao</creatorcontrib><creatorcontrib>Shi, Wei-Yu</creatorcontrib><creatorcontrib>Huang, Yan-Chong</creatorcontrib><creatorcontrib>Liu, Xue-Yuan</creatorcontrib><creatorcontrib>Liang, Yong-Min</creatorcontrib><title>Site-selective coupling of remote C(sp 3 )-H/ meta -C(sp 2 )-H bonds enabled by Ru/photoredox dual catalysis and mechanistic studies</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>Construction of C(sp
)-C(sp
) bonds
regioselective coupling of C(sp
)-H/C(sp
)-H bonds is challenging due to the low reactivity and regioselectivity of C-H bonds. Here, a novel photoinduced Ru/photocatalyst-cocatalyzed regioselective cross-dehydrogenative coupling of dual remote C-H bonds, including inert γ-C(sp
)-H bonds in amides and
-C(sp
)-H bonds in arenes, to construct
-alkylated arenes has been accomplished. This metallaphotoredox-enabled site-selective coupling between remote inert C(sp
)-H bonds and
-C(sp
)-H bonds is characterized by its unique site-selectivity, redox-neutral conditions, broad substrate scope and wide use of late-stage functionalization of bioactive molecules. Moreover, this reaction represents a novel case of regioselective cross-dehydrogenative coupling of unactivated alkanes and arenes
a new catalytic process and provides a new strategy for
-functionalized arenes under mild reaction conditions. Density functional theory (DFT) calculations and control experiments explained the site-selectivity and the detailed mechanism of this reaction.</description><subject>Alkanes</subject><subject>Alkylation</subject><subject>Amides</subject><subject>Aromatic compounds</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Coupling (molecular)</subject><subject>Dehydrogenation</subject><subject>Density functional theory</subject><subject>Regioselectivity</subject><subject>Selectivity</subject><subject>Substrates</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkU2LFDEQhoMo7jLuxR8gAS-7QjvpZJLuXIRl_FhhQXD1HNJJZSdLutMm6cW5-8PNfjioVYcqqh5eqngRetmSty1hcm1pNoR0YqOfoGNKNm0jOJNPDz0lR-gk5xtSg7GW0-45OmJccM4FPUa_rnyBJkMAU_wtYBOXOfjpGkeHE4yxAN6e5hkzfNZcrPEIRePmfkLvJniIk80YJj0EsHjY46_Let7FEhPY-BPbRQdsdNFhn33GerJVwuz05HPxBueyWA_5BXrmdMhw8lhX6PvHD9-2F83ll0-ft-eXjWFMlEYQSa2RIFvhwBhpXe-o6aUdpGad7ZjpaMf1Rg9OO6HboZemt5QCd9yJ-v4KvXvQnZdhBGtgKkkHNSc_6rRXUXv172byO3Udb5UkkrU1V-j0USDFHwvkokafDYSgJ4hLVlR0jPF-I2lFX_-H3sQlTfW9SolqDuFEVOrNA2VSzDmBOxzTEnXnr3pPr7b3_p5X-NXf5x_QP26y3yT7oGo</recordid><startdate>20220511</startdate><enddate>20220511</enddate><creator>Liu, Hong-Chao</creator><creator>Kong, Xiangtao</creator><creator>Gong, Xiao-Ping</creator><creator>Li, Yuke</creator><creator>Niu, Zhi-Jie</creator><creator>Gou, Xue-Ya</creator><creator>Li, Xue-Song</creator><creator>Wang, Yu-Zhao</creator><creator>Shi, Wei-Yu</creator><creator>Huang, Yan-Chong</creator><creator>Liu, Xue-Yuan</creator><creator>Liang, Yong-Min</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-8280-8211</orcidid><orcidid>https://orcid.org/0000-0003-0162-5072</orcidid><orcidid>https://orcid.org/0000-0002-8862-9924</orcidid></search><sort><creationdate>20220511</creationdate><title>Site-selective coupling of remote C(sp 3 )-H/ meta -C(sp 2 )-H bonds enabled by Ru/photoredox dual catalysis and mechanistic studies</title><author>Liu, Hong-Chao ; Kong, Xiangtao ; Gong, Xiao-Ping ; Li, Yuke ; Niu, Zhi-Jie ; Gou, Xue-Ya ; Li, Xue-Song ; Wang, Yu-Zhao ; Shi, Wei-Yu ; Huang, Yan-Chong ; Liu, Xue-Yuan ; Liang, Yong-Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c336t-6092dc9e916fecc9df8f2c89db9a37d73c7275a4abfaf6a1b89c8d22e5f5f6003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkanes</topic><topic>Alkylation</topic><topic>Amides</topic><topic>Aromatic compounds</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Coupling (molecular)</topic><topic>Dehydrogenation</topic><topic>Density functional theory</topic><topic>Regioselectivity</topic><topic>Selectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Hong-Chao</creatorcontrib><creatorcontrib>Kong, Xiangtao</creatorcontrib><creatorcontrib>Gong, Xiao-Ping</creatorcontrib><creatorcontrib>Li, Yuke</creatorcontrib><creatorcontrib>Niu, Zhi-Jie</creatorcontrib><creatorcontrib>Gou, Xue-Ya</creatorcontrib><creatorcontrib>Li, Xue-Song</creatorcontrib><creatorcontrib>Wang, Yu-Zhao</creatorcontrib><creatorcontrib>Shi, Wei-Yu</creatorcontrib><creatorcontrib>Huang, Yan-Chong</creatorcontrib><creatorcontrib>Liu, Xue-Yuan</creatorcontrib><creatorcontrib>Liang, Yong-Min</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Hong-Chao</au><au>Kong, Xiangtao</au><au>Gong, Xiao-Ping</au><au>Li, Yuke</au><au>Niu, Zhi-Jie</au><au>Gou, Xue-Ya</au><au>Li, Xue-Song</au><au>Wang, Yu-Zhao</au><au>Shi, Wei-Yu</au><au>Huang, Yan-Chong</au><au>Liu, Xue-Yuan</au><au>Liang, Yong-Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Site-selective coupling of remote C(sp 3 )-H/ meta -C(sp 2 )-H bonds enabled by Ru/photoredox dual catalysis and mechanistic studies</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2022-05-11</date><risdate>2022</risdate><volume>13</volume><issue>18</issue><spage>5382</spage><epage>5389</epage><pages>5382-5389</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Construction of C(sp
)-C(sp
) bonds
regioselective coupling of C(sp
)-H/C(sp
)-H bonds is challenging due to the low reactivity and regioselectivity of C-H bonds. Here, a novel photoinduced Ru/photocatalyst-cocatalyzed regioselective cross-dehydrogenative coupling of dual remote C-H bonds, including inert γ-C(sp
)-H bonds in amides and
-C(sp
)-H bonds in arenes, to construct
-alkylated arenes has been accomplished. This metallaphotoredox-enabled site-selective coupling between remote inert C(sp
)-H bonds and
-C(sp
)-H bonds is characterized by its unique site-selectivity, redox-neutral conditions, broad substrate scope and wide use of late-stage functionalization of bioactive molecules. Moreover, this reaction represents a novel case of regioselective cross-dehydrogenative coupling of unactivated alkanes and arenes
a new catalytic process and provides a new strategy for
-functionalized arenes under mild reaction conditions. Density functional theory (DFT) calculations and control experiments explained the site-selectivity and the detailed mechanism of this reaction.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35655562</pmid><doi>10.1039/d2sc00764a</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-8280-8211</orcidid><orcidid>https://orcid.org/0000-0003-0162-5072</orcidid><orcidid>https://orcid.org/0000-0002-8862-9924</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2022-05, Vol.13 (18), p.5382-5389 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9093131 |
| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Alkanes Alkylation Amides Aromatic compounds Catalysis Chemistry Coupling (molecular) Dehydrogenation Density functional theory Regioselectivity Selectivity Substrates |
| title | Site-selective coupling of remote C(sp 3 )-H/ meta -C(sp 2 )-H bonds enabled by Ru/photoredox dual catalysis and mechanistic studies |
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