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Photo-induced radical borylation of hemiacetals via C–C bond cleavage
In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal...
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Published in: | Tetrahedron 2021-01, Vol.80, p.131867, Article 131867 |
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creator | Liu, Qianyi Zhang, Jianning Zhang, Lei Mo, Fanyang |
description | In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.
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doi_str_mv | 10.1016/j.tet.2020.131867 |
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[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2020.131867</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Borylation ; C–C bond Cleavage ; Hemiacetal ; Photocatalysis</subject><ispartof>Tetrahedron, 2021-01, Vol.80, p.131867, Article 131867</ispartof><rights>2020 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-a92bf51c8a0b01658bfc64db118074d2c52a2c66eebc9e54f33466a632de5dd3</citedby><cites>FETCH-LOGICAL-c363t-a92bf51c8a0b01658bfc64db118074d2c52a2c66eebc9e54f33466a632de5dd3</cites><orcidid>0000-0002-4140-3020</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Liu, Qianyi</creatorcontrib><creatorcontrib>Zhang, Jianning</creatorcontrib><creatorcontrib>Zhang, Lei</creatorcontrib><creatorcontrib>Mo, Fanyang</creatorcontrib><title>Photo-induced radical borylation of hemiacetals via C–C bond cleavage</title><title>Tetrahedron</title><description>In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.
[Display omitted]</description><subject>Borylation</subject><subject>C–C bond Cleavage</subject><subject>Hemiacetal</subject><subject>Photocatalysis</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kEFOwzAQRS0EEqVwAHa-QIrHdtxUrFAEBakSLLq3HHtCHaUxckyl7rgDN-QkuAprVqPRnz_6_xFyC2wBDNRdt0iYFpzxvAuo1PKMzEAqWZQS1DmZMSZZIbN8Sa7GsWOMAXAxI-u3XUih8IP7tOhoNM5b09MmxGNvkg8DDS3d4d4bi8n0Iz14Q-ufr-863wyO2h7NwbzjNblos4w3f3NOtk-P2_q52LyuX-qHTWGFEqkwK960JdjKsCbHLqumtUq6BqBiS-m4LbnhVinExq6wlK0QUimjBHdYOifmBKa3NoZxjNjqj-j3Jh41MH0CoTudQegTCD2ByJ77yYM518Fj1KP1OOS6PqJN2gX_j_sXfktnHg</recordid><startdate>20210129</startdate><enddate>20210129</enddate><creator>Liu, Qianyi</creator><creator>Zhang, Jianning</creator><creator>Zhang, Lei</creator><creator>Mo, Fanyang</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-4140-3020</orcidid></search><sort><creationdate>20210129</creationdate><title>Photo-induced radical borylation of hemiacetals via C–C bond cleavage</title><author>Liu, Qianyi ; Zhang, Jianning ; Zhang, Lei ; Mo, Fanyang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-a92bf51c8a0b01658bfc64db118074d2c52a2c66eebc9e54f33466a632de5dd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Borylation</topic><topic>C–C bond Cleavage</topic><topic>Hemiacetal</topic><topic>Photocatalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Qianyi</creatorcontrib><creatorcontrib>Zhang, Jianning</creatorcontrib><creatorcontrib>Zhang, Lei</creatorcontrib><creatorcontrib>Mo, Fanyang</creatorcontrib><collection>CrossRef</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Qianyi</au><au>Zhang, Jianning</au><au>Zhang, Lei</au><au>Mo, Fanyang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photo-induced radical borylation of hemiacetals via C–C bond cleavage</atitle><jtitle>Tetrahedron</jtitle><date>2021-01-29</date><risdate>2021</risdate><volume>80</volume><spage>131867</spage><pages>131867-</pages><artnum>131867</artnum><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.
[Display omitted]</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2020.131867</doi><orcidid>https://orcid.org/0000-0002-4140-3020</orcidid></addata></record> |
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subjects | Borylation C–C bond Cleavage Hemiacetal Photocatalysis |
title | Photo-induced radical borylation of hemiacetals via C–C bond cleavage |
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