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Organocatalytic C−H Functionalization of Simple Alkanes
The direct functionalization of inert C(sp 3 )‐H bonds to form carbon‐carbon and carbon‐heteroatom bonds offers vast potential for chemical synthesis and therefore receives increasing attention. At present, most successes come from strategies using metal catalysts/reagents or photo/electrochemical p...
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| Published in: | Angewandte Chemie 2023-11, Vol.135 (45) |
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| Main Authors: | , , , , , , , , |
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| container_issue | 45 |
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| container_title | Angewandte Chemie |
| container_volume | 135 |
| creator | Su, Fen Lu, Fengfei Tang, Kun Lv, Xiaokang Luo, Zhongfu Che, Fengrui Long, Hongyan Wu, Xingxing Chi, Yonggui Robin |
| description | The direct functionalization of inert C(sp
3
)‐H bonds to form carbon‐carbon and carbon‐heteroatom bonds offers vast potential for chemical synthesis and therefore receives increasing attention. At present, most successes come from strategies using metal catalysts/reagents or photo/electrochemical processes. The use of organocatalysis for this purpose remains scarce, especially when dealing with challenging C−H bonds such as those from simple alkanes. Here we disclose the first organocatalytic direct functionalization/acylation of inert C(sp
3
)‐H bonds of completely unfunctionalized alkanes. Our approach involves N‐heterocyclic carbene catalyst‐mediated carbonyl radical intermediate generation and coupling with simple alkanes (through the corresponding alkyl radical intermediates generated via a hydrogen atom transfer process). Unreactive C−H bonds are widely present in fossil fuel feedstocks, commercially important organic polymers, and complex molecules such as natural products. Our present study shall inspire a new avenue for quick functionalization of these molecules under the light‐ and metal‐free catalytic conditions. |
| doi_str_mv | 10.1002/ange.202310072 |
| format | article |
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3
)‐H bonds to form carbon‐carbon and carbon‐heteroatom bonds offers vast potential for chemical synthesis and therefore receives increasing attention. At present, most successes come from strategies using metal catalysts/reagents or photo/electrochemical processes. The use of organocatalysis for this purpose remains scarce, especially when dealing with challenging C−H bonds such as those from simple alkanes. Here we disclose the first organocatalytic direct functionalization/acylation of inert C(sp
3
)‐H bonds of completely unfunctionalized alkanes. Our approach involves N‐heterocyclic carbene catalyst‐mediated carbonyl radical intermediate generation and coupling with simple alkanes (through the corresponding alkyl radical intermediates generated via a hydrogen atom transfer process). Unreactive C−H bonds are widely present in fossil fuel feedstocks, commercially important organic polymers, and complex molecules such as natural products. Our present study shall inspire a new avenue for quick functionalization of these molecules under the light‐ and metal‐free catalytic conditions.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.202310072</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Acylation ; Alkanes ; Carbon ; Carbonyl compounds ; Carbonyls ; Catalysts ; Chemical synthesis ; Chemistry ; Electrochemistry ; Fossil fuels ; Hydrogen atoms ; Intermediates ; Natural products ; Polymers ; Radicals ; Reagents</subject><ispartof>Angewandte Chemie, 2023-11, Vol.135 (45)</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1072-8a03b90befca106977ed06b9ea6b3d438862ba63fbbd7e2221be058ba4159c23</cites><orcidid>0000-0003-0573-257X ; 0000-0002-6281-243X</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>Su, Fen</creatorcontrib><creatorcontrib>Lu, Fengfei</creatorcontrib><creatorcontrib>Tang, Kun</creatorcontrib><creatorcontrib>Lv, Xiaokang</creatorcontrib><creatorcontrib>Luo, Zhongfu</creatorcontrib><creatorcontrib>Che, Fengrui</creatorcontrib><creatorcontrib>Long, Hongyan</creatorcontrib><creatorcontrib>Wu, Xingxing</creatorcontrib><creatorcontrib>Chi, Yonggui Robin</creatorcontrib><title>Organocatalytic C−H Functionalization of Simple Alkanes</title><title>Angewandte Chemie</title><description>The direct functionalization of inert C(sp
3
)‐H bonds to form carbon‐carbon and carbon‐heteroatom bonds offers vast potential for chemical synthesis and therefore receives increasing attention. At present, most successes come from strategies using metal catalysts/reagents or photo/electrochemical processes. The use of organocatalysis for this purpose remains scarce, especially when dealing with challenging C−H bonds such as those from simple alkanes. Here we disclose the first organocatalytic direct functionalization/acylation of inert C(sp
3
)‐H bonds of completely unfunctionalized alkanes. Our approach involves N‐heterocyclic carbene catalyst‐mediated carbonyl radical intermediate generation and coupling with simple alkanes (through the corresponding alkyl radical intermediates generated via a hydrogen atom transfer process). Unreactive C−H bonds are widely present in fossil fuel feedstocks, commercially important organic polymers, and complex molecules such as natural products. Our present study shall inspire a new avenue for quick functionalization of these molecules under the light‐ and metal‐free catalytic conditions.</description><subject>Acylation</subject><subject>Alkanes</subject><subject>Carbon</subject><subject>Carbonyl compounds</subject><subject>Carbonyls</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Electrochemistry</subject><subject>Fossil fuels</subject><subject>Hydrogen atoms</subject><subject>Intermediates</subject><subject>Natural products</subject><subject>Polymers</subject><subject>Radicals</subject><subject>Reagents</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNo9kM1OwzAQhC0EEqFw5RyJc8raTvxzrCpKkSr1QO_W2nWqlDQJdnooT8CZR-RJmqiI085Ko9HMR8gjhSkFYM_Y7PyUAePDJ9kVSWjBaMZlIa9JApDnmWK5viV3Me4BQDCpE6LXYYdN67DH-tRXLp3_fv8s08WxcX3VNlhXXziKtC3T9-rQ1T6d1R_Y-HhPbkqso3_4uxOyWbxs5ststX59m89WmaNDjUwhcKvB-tIhBaGl9FsQVnsUlm9zrpRgFgUvrd1Kzxij1kOhLOa00I7xCXm6xHah_Tz62Jt9ewxDsWiYUsMGkcvRNb24XGhjDL40XagOGE6GghnpmJGO-afDz6EsWEM</recordid><startdate>20231106</startdate><enddate>20231106</enddate><creator>Su, Fen</creator><creator>Lu, Fengfei</creator><creator>Tang, Kun</creator><creator>Lv, Xiaokang</creator><creator>Luo, Zhongfu</creator><creator>Che, Fengrui</creator><creator>Long, Hongyan</creator><creator>Wu, Xingxing</creator><creator>Chi, Yonggui Robin</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-0573-257X</orcidid><orcidid>https://orcid.org/0000-0002-6281-243X</orcidid></search><sort><creationdate>20231106</creationdate><title>Organocatalytic C−H Functionalization of Simple Alkanes</title><author>Su, Fen ; Lu, Fengfei ; Tang, Kun ; Lv, Xiaokang ; Luo, Zhongfu ; Che, Fengrui ; Long, Hongyan ; Wu, Xingxing ; Chi, Yonggui Robin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1072-8a03b90befca106977ed06b9ea6b3d438862ba63fbbd7e2221be058ba4159c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acylation</topic><topic>Alkanes</topic><topic>Carbon</topic><topic>Carbonyl compounds</topic><topic>Carbonyls</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Electrochemistry</topic><topic>Fossil fuels</topic><topic>Hydrogen atoms</topic><topic>Intermediates</topic><topic>Natural products</topic><topic>Polymers</topic><topic>Radicals</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Su, Fen</creatorcontrib><creatorcontrib>Lu, Fengfei</creatorcontrib><creatorcontrib>Tang, Kun</creatorcontrib><creatorcontrib>Lv, Xiaokang</creatorcontrib><creatorcontrib>Luo, Zhongfu</creatorcontrib><creatorcontrib>Che, Fengrui</creatorcontrib><creatorcontrib>Long, Hongyan</creatorcontrib><creatorcontrib>Wu, Xingxing</creatorcontrib><creatorcontrib>Chi, Yonggui Robin</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Su, Fen</au><au>Lu, Fengfei</au><au>Tang, Kun</au><au>Lv, Xiaokang</au><au>Luo, Zhongfu</au><au>Che, Fengrui</au><au>Long, Hongyan</au><au>Wu, Xingxing</au><au>Chi, Yonggui Robin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organocatalytic C−H Functionalization of Simple Alkanes</atitle><jtitle>Angewandte Chemie</jtitle><date>2023-11-06</date><risdate>2023</risdate><volume>135</volume><issue>45</issue><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The direct functionalization of inert C(sp
3
)‐H bonds to form carbon‐carbon and carbon‐heteroatom bonds offers vast potential for chemical synthesis and therefore receives increasing attention. At present, most successes come from strategies using metal catalysts/reagents or photo/electrochemical processes. The use of organocatalysis for this purpose remains scarce, especially when dealing with challenging C−H bonds such as those from simple alkanes. Here we disclose the first organocatalytic direct functionalization/acylation of inert C(sp
3
)‐H bonds of completely unfunctionalized alkanes. Our approach involves N‐heterocyclic carbene catalyst‐mediated carbonyl radical intermediate generation and coupling with simple alkanes (through the corresponding alkyl radical intermediates generated via a hydrogen atom transfer process). Unreactive C−H bonds are widely present in fossil fuel feedstocks, commercially important organic polymers, and complex molecules such as natural products. Our present study shall inspire a new avenue for quick functionalization of these molecules under the light‐ and metal‐free catalytic conditions.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.202310072</doi><orcidid>https://orcid.org/0000-0003-0573-257X</orcidid><orcidid>https://orcid.org/0000-0002-6281-243X</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | Wiley |
| subjects | Acylation Alkanes Carbon Carbonyl compounds Carbonyls Catalysts Chemical synthesis Chemistry Electrochemistry Fossil fuels Hydrogen atoms Intermediates Natural products Polymers Radicals Reagents |
| title | Organocatalytic C−H Functionalization of Simple Alkanes |
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