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Transition metal-free visible light photoredox-catalyzed remote C(sp3)−H borylation enabled by 1,5-hydrogen atom transfer
The borylation of unreactive carbon-hydrogen bonds is a valuable method for transforming feedstock chemicals into versatile building blocks. Here, we describe a transition metal-free method for the photoredox-catalyzed borylation of unactivated C(sp 3 )−H bond, initiated by 1,5-hydrogen atom transfe...
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| Published in: | Communications chemistry 2023-07, Vol.6 (1), p.156-156, Article 156 |
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| cites | cdi_FETCH-LOGICAL-c541t-52291a405931dbee730fd0c7b1cc727a5110533d68da0391376155c82b24cda23 |
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| container_title | Communications chemistry |
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| creator | Sun, Beiqi Li, Wenke Liu, Qianyi Zhang, Gaoge Mo, Fanyang |
| description | The borylation of unreactive carbon-hydrogen bonds is a valuable method for transforming feedstock chemicals into versatile building blocks. Here, we describe a transition metal-free method for the photoredox-catalyzed borylation of unactivated C(sp
3
)−H bond, initiated by 1,5-hydrogen atom transfer (HAT). The remote borylation was directed by 1,5-HAT of the amidyl radical, which was generated by photocatalytic reduction of hydroxamic acid derivatives. The method accommodates substrates with primary, secondary and tertiary C(sp
3
)−H bonds, yielding moderate to good product yields (up to 92%) with tolerance for various functional groups. Mechanistic studies, including radical clock experiments and DFT calculations, provided detailed insight into the 1,5-HAT borylation process.
Alkyl boronic esters are commonly used building blocks in organic synthesis, causing efficient C-H borylation methods to be in high demand. Here, the authors develop a method for the photoredox-catalyzed borylation of unreactive C(sp
3
)-H bonds, mediated by amidyl radicals to achieve C-H borylation at the
λ
position of carbonyl compounds. |
| doi_str_mv | 10.1038/s42004-023-00960-z |
| format | article |
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3
)−H bond, initiated by 1,5-hydrogen atom transfer (HAT). The remote borylation was directed by 1,5-HAT of the amidyl radical, which was generated by photocatalytic reduction of hydroxamic acid derivatives. The method accommodates substrates with primary, secondary and tertiary C(sp
3
)−H bonds, yielding moderate to good product yields (up to 92%) with tolerance for various functional groups. Mechanistic studies, including radical clock experiments and DFT calculations, provided detailed insight into the 1,5-HAT borylation process.
Alkyl boronic esters are commonly used building blocks in organic synthesis, causing efficient C-H borylation methods to be in high demand. Here, the authors develop a method for the photoredox-catalyzed borylation of unreactive C(sp
3
)-H bonds, mediated by amidyl radicals to achieve C-H borylation at the
λ
position of carbonyl compounds.</description><identifier>ISSN: 2399-3669</identifier><identifier>EISSN: 2399-3669</identifier><identifier>DOI: 10.1038/s42004-023-00960-z</identifier><identifier>PMID: 37488210</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>639/638/403/933 ; 639/638/439/890 ; 639/638/77/888 ; Carbon ; Carbonyl compounds ; Carbonyls ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Esters ; Functional groups ; Hydrogen ; Hydrogen atoms ; Hydrogen bonds ; Light ; Nitrogen ; Photocatalysis ; Photoredox catalysis ; Radicals ; Substrates ; Transition metals</subject><ispartof>Communications chemistry, 2023-07, Vol.6 (1), p.156-156, Article 156</ispartof><rights>The Author(s) 2023</rights><rights>2023. The Author(s).</rights><rights>The Author(s) 2023. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c541t-52291a405931dbee730fd0c7b1cc727a5110533d68da0391376155c82b24cda23</citedby><cites>FETCH-LOGICAL-c541t-52291a405931dbee730fd0c7b1cc727a5110533d68da0391376155c82b24cda23</cites><orcidid>0000-0002-4140-3020</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/PMC10366130/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2841215005?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37488210$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sun, Beiqi</creatorcontrib><creatorcontrib>Li, Wenke</creatorcontrib><creatorcontrib>Liu, Qianyi</creatorcontrib><creatorcontrib>Zhang, Gaoge</creatorcontrib><creatorcontrib>Mo, Fanyang</creatorcontrib><title>Transition metal-free visible light photoredox-catalyzed remote C(sp3)−H borylation enabled by 1,5-hydrogen atom transfer</title><title>Communications chemistry</title><addtitle>Commun Chem</addtitle><addtitle>Commun Chem</addtitle><description>The borylation of unreactive carbon-hydrogen bonds is a valuable method for transforming feedstock chemicals into versatile building blocks. Here, we describe a transition metal-free method for the photoredox-catalyzed borylation of unactivated C(sp
3
)−H bond, initiated by 1,5-hydrogen atom transfer (HAT). The remote borylation was directed by 1,5-HAT of the amidyl radical, which was generated by photocatalytic reduction of hydroxamic acid derivatives. The method accommodates substrates with primary, secondary and tertiary C(sp
3
)−H bonds, yielding moderate to good product yields (up to 92%) with tolerance for various functional groups. Mechanistic studies, including radical clock experiments and DFT calculations, provided detailed insight into the 1,5-HAT borylation process.
Alkyl boronic esters are commonly used building blocks in organic synthesis, causing efficient C-H borylation methods to be in high demand. Here, the authors develop a method for the photoredox-catalyzed borylation of unreactive C(sp
3
)-H bonds, mediated by amidyl radicals to achieve C-H borylation at the
λ
position of carbonyl compounds.</description><subject>639/638/403/933</subject><subject>639/638/439/890</subject><subject>639/638/77/888</subject><subject>Carbon</subject><subject>Carbonyl compounds</subject><subject>Carbonyls</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Esters</subject><subject>Functional groups</subject><subject>Hydrogen</subject><subject>Hydrogen atoms</subject><subject>Hydrogen bonds</subject><subject>Light</subject><subject>Nitrogen</subject><subject>Photocatalysis</subject><subject>Photoredox catalysis</subject><subject>Radicals</subject><subject>Substrates</subject><subject>Transition metals</subject><issn>2399-3669</issn><issn>2399-3669</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNp9ksFu1DAQhi0EotXSF-CALHEpEoGxncTxCaEV0EqVuJSz5diT3aySeLGzFVlegDOPyJPg3ZTScuBky_PP93vsn5DnDN4wENXbmHOAPAMuMgBVQrZ_RE65UCoTZake39ufkLMYNwDAgQkpq6fkRMi8qjiDU_L9OpghtmPrB9rjaLqsCYj0po1t3SHt2tV6pNu1H31A579l1iTNtEdHA_Z-RLo8j1vx6tePnxe09mHqzBGFg0ntjtYTZa-LbD254Fc4UDP6no4HywbDM_KkMV3Es9t1Qb58_HC9vMiuPn-6XL6_ymyRszErOFfM5FAowVyNKAU0DqysmbWSS1MwBoUQrqycAaHSjCUrClvxmufWGS4W5HLmOm82ehva3oRJe9Pq44EPK23C2NoOtbKlzCUKJazIpVWGWc54zQBYqawQifVuZm13dY_O4pCm6R5AH1aGdq1X_kanTytLJiARzm8JwX_dYRx130aLXWcG9LuoeZWzSqqCH8xe_iPd-F0Y0lsdVZwVkCZfED6rbPAxBmzubsPgYFvpOSs6ZUUfs6L3qenF_TnuWv4kIwnELIipNKww_PX-D_Y3OibKtw</recordid><startdate>20230724</startdate><enddate>20230724</enddate><creator>Sun, Beiqi</creator><creator>Li, Wenke</creator><creator>Liu, Qianyi</creator><creator>Zhang, Gaoge</creator><creator>Mo, Fanyang</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><general>Nature Portfolio</general><scope>C6C</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>8FE</scope><scope>8FG</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>HCIFZ</scope><scope>KB.</scope><scope>L6V</scope><scope>M7S</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PTHSS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-4140-3020</orcidid></search><sort><creationdate>20230724</creationdate><title>Transition metal-free visible light photoredox-catalyzed remote C(sp3)−H borylation enabled by 1,5-hydrogen atom transfer</title><author>Sun, Beiqi ; Li, Wenke ; Liu, Qianyi ; Zhang, Gaoge ; Mo, Fanyang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c541t-52291a405931dbee730fd0c7b1cc727a5110533d68da0391376155c82b24cda23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>639/638/403/933</topic><topic>639/638/439/890</topic><topic>639/638/77/888</topic><topic>Carbon</topic><topic>Carbonyl compounds</topic><topic>Carbonyls</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Esters</topic><topic>Functional groups</topic><topic>Hydrogen</topic><topic>Hydrogen atoms</topic><topic>Hydrogen bonds</topic><topic>Light</topic><topic>Nitrogen</topic><topic>Photocatalysis</topic><topic>Photoredox catalysis</topic><topic>Radicals</topic><topic>Substrates</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Beiqi</creatorcontrib><creatorcontrib>Li, Wenke</creatorcontrib><creatorcontrib>Liu, Qianyi</creatorcontrib><creatorcontrib>Zhang, Gaoge</creatorcontrib><creatorcontrib>Mo, Fanyang</creatorcontrib><collection>SpringerOpen(OpenAccess)</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>SciTech Premium Collection</collection><collection>Materials Science Database</collection><collection>ProQuest Engineering Collection</collection><collection>Engineering Database</collection><collection>Materials science collection</collection><collection>ProQuest - Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>Engineering collection</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Communications chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Beiqi</au><au>Li, Wenke</au><au>Liu, Qianyi</au><au>Zhang, Gaoge</au><au>Mo, Fanyang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition metal-free visible light photoredox-catalyzed remote C(sp3)−H borylation enabled by 1,5-hydrogen atom transfer</atitle><jtitle>Communications chemistry</jtitle><stitle>Commun Chem</stitle><addtitle>Commun Chem</addtitle><date>2023-07-24</date><risdate>2023</risdate><volume>6</volume><issue>1</issue><spage>156</spage><epage>156</epage><pages>156-156</pages><artnum>156</artnum><issn>2399-3669</issn><eissn>2399-3669</eissn><abstract>The borylation of unreactive carbon-hydrogen bonds is a valuable method for transforming feedstock chemicals into versatile building blocks. Here, we describe a transition metal-free method for the photoredox-catalyzed borylation of unactivated C(sp
3
)−H bond, initiated by 1,5-hydrogen atom transfer (HAT). The remote borylation was directed by 1,5-HAT of the amidyl radical, which was generated by photocatalytic reduction of hydroxamic acid derivatives. The method accommodates substrates with primary, secondary and tertiary C(sp
3
)−H bonds, yielding moderate to good product yields (up to 92%) with tolerance for various functional groups. Mechanistic studies, including radical clock experiments and DFT calculations, provided detailed insight into the 1,5-HAT borylation process.
Alkyl boronic esters are commonly used building blocks in organic synthesis, causing efficient C-H borylation methods to be in high demand. Here, the authors develop a method for the photoredox-catalyzed borylation of unreactive C(sp
3
)-H bonds, mediated by amidyl radicals to achieve C-H borylation at the
λ
position of carbonyl compounds.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>37488210</pmid><doi>10.1038/s42004-023-00960-z</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-4140-3020</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Communications chemistry, 2023-07, Vol.6 (1), p.156-156, Article 156 |
| issn | 2399-3669 2399-3669 |
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| subjects | 639/638/403/933 639/638/439/890 639/638/77/888 Carbon Carbonyl compounds Carbonyls Chemistry Chemistry and Materials Science Chemistry/Food Science Esters Functional groups Hydrogen Hydrogen atoms Hydrogen bonds Light Nitrogen Photocatalysis Photoredox catalysis Radicals Substrates Transition metals |
| title | Transition metal-free visible light photoredox-catalyzed remote C(sp3)−H borylation enabled by 1,5-hydrogen atom transfer |
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