Visible light-mediated metal-free alkyl Suzuki-Miyaura coupling of alkyl halides and alkenylboronic acids/esters: a green method for the synthesis of allyl difluoride derivatives
The Suzuki-Miyaura reaction has greatly facilitated the construction of C-C bonds and is well appreciated in medicinal chemistry, yet transition metal residues in this process are an unavoidable challenge. Herein, we report the first visible-light-driven photocatalyst-free coupling reaction of alken...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2023-05, Vol.25 (9), p.3453-3461 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Qu, Chuan-Hua Yan, Xiao Li, Shu-Ting Liu, Jian-Bo Xu, Zhi-Gang Chen, Zhong-Zhu Tang, Dian-Yong Liu, Huan-Xiang Song, Gui-Ting |
| description | The Suzuki-Miyaura reaction has greatly facilitated the construction of C-C bonds and is well appreciated in medicinal chemistry, yet transition metal residues in this process are an unavoidable challenge. Herein, we report the first visible-light-driven photocatalyst-free coupling reaction of alkenylboronic acids/esters with α-bromodifluoroacylarenes, providing streamlining access to a series of Suzuki coupling products. The reactions proceed under metal-free conditions with a wide substrate scope. Mechanistic experiments and DFT calculation studies revealed that halogen bonding interactions, mainly generated
in situ
between α-bromodifluoroacylarenes and tertiary amines, could promote the C
sp
3
-Br bond homolytic cleavage from difluorobromoaryl ketones.
Halogen bonding-assisted C
sp
3
-Br homolysis and bromine radical-mediated oxidative deboronation make visible-light-driven photocatalyst-free alkyl Suzuki-Miyaura coupling of alkenylboronic acids/esters with α-bromodifluoroacylarenes accessible. |
| doi_str_mv | 10.1039/d3gc00368j |
| format | Article |
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in situ
between α-bromodifluoroacylarenes and tertiary amines, could promote the C
sp
3
-Br bond homolytic cleavage from difluorobromoaryl ketones.
Halogen bonding-assisted C
sp
3
-Br homolysis and bromine radical-mediated oxidative deboronation make visible-light-driven photocatalyst-free alkyl Suzuki-Miyaura coupling of alkenylboronic acids/esters with α-bromodifluoroacylarenes accessible.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/d3gc00368j</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Amines ; Chemical reactions ; Coupling ; Covalent bonds ; Difluorides ; Esters ; Green chemistry ; Halides ; Ketones ; Streamlining ; Substrates ; Transition metals</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2023-05, Vol.25 (9), p.3453-3461</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-72eae4918bc7e703ebb005ad3fd1dd8d6c3bc6c7a0e09833f8847f01dd06cb723</citedby><cites>FETCH-LOGICAL-c281t-72eae4918bc7e703ebb005ad3fd1dd8d6c3bc6c7a0e09833f8847f01dd06cb723</cites><orcidid>0000-0002-3821-3963 ; 0000-0001-9389-870X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Qu, Chuan-Hua</creatorcontrib><creatorcontrib>Yan, Xiao</creatorcontrib><creatorcontrib>Li, Shu-Ting</creatorcontrib><creatorcontrib>Liu, Jian-Bo</creatorcontrib><creatorcontrib>Xu, Zhi-Gang</creatorcontrib><creatorcontrib>Chen, Zhong-Zhu</creatorcontrib><creatorcontrib>Tang, Dian-Yong</creatorcontrib><creatorcontrib>Liu, Huan-Xiang</creatorcontrib><creatorcontrib>Song, Gui-Ting</creatorcontrib><title>Visible light-mediated metal-free alkyl Suzuki-Miyaura coupling of alkyl halides and alkenylboronic acids/esters: a green method for the synthesis of allyl difluoride derivatives</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>The Suzuki-Miyaura reaction has greatly facilitated the construction of C-C bonds and is well appreciated in medicinal chemistry, yet transition metal residues in this process are an unavoidable challenge. Herein, we report the first visible-light-driven photocatalyst-free coupling reaction of alkenylboronic acids/esters with α-bromodifluoroacylarenes, providing streamlining access to a series of Suzuki coupling products. The reactions proceed under metal-free conditions with a wide substrate scope. Mechanistic experiments and DFT calculation studies revealed that halogen bonding interactions, mainly generated
in situ
between α-bromodifluoroacylarenes and tertiary amines, could promote the C
sp
3
-Br bond homolytic cleavage from difluorobromoaryl ketones.
Halogen bonding-assisted C
sp
3
-Br homolysis and bromine radical-mediated oxidative deboronation make visible-light-driven photocatalyst-free alkyl Suzuki-Miyaura coupling of alkenylboronic acids/esters with α-bromodifluoroacylarenes accessible.</description><subject>Amines</subject><subject>Chemical reactions</subject><subject>Coupling</subject><subject>Covalent bonds</subject><subject>Difluorides</subject><subject>Esters</subject><subject>Green chemistry</subject><subject>Halides</subject><subject>Ketones</subject><subject>Streamlining</subject><subject>Substrates</subject><subject>Transition metals</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpFkV1LwzAUhosoOKc33gsB74S6pKn98E6mTmXihR-3JU1OumxZM5N2UH-Wv9DUyrw6IXl43kPeIDgl-JJgmk8ErTjGNMmWe8GIxAkN8yjF-7tzEh0GR84tMSYkTeJR8P2hnCo1IK2qRROuQSjWgEBraJgOpQVATK86jV7br3alwmfVsdYyxE270aqukJF_wIJpJcAhVov-BupOl8aaWnHEuBJuAq4B664RQ5XX1n3EwggkjUXNApDraj-ccoNSe6VQUrfGei0SYNWWNWoL7jg4kEw7OPmb4-D9_u5t-hDOX2aP05t5yKOMNGEaAYM4J1nJU0gxhbLE-IoJKgURIhMJpyVPeMow4DyjVGZZnErs33DCyzSi4-B88G6s-Wz99sXStLb2kYUP8P9HsrynLgaKW-OcBVlsrFoz2xUEF30nxS2dTX87efLw2QBbx3fcf2f0Bz4tjb0</recordid><startdate>20230509</startdate><enddate>20230509</enddate><creator>Qu, Chuan-Hua</creator><creator>Yan, Xiao</creator><creator>Li, Shu-Ting</creator><creator>Liu, Jian-Bo</creator><creator>Xu, Zhi-Gang</creator><creator>Chen, Zhong-Zhu</creator><creator>Tang, Dian-Yong</creator><creator>Liu, Huan-Xiang</creator><creator>Song, Gui-Ting</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/0000-0002-3821-3963</orcidid><orcidid>https://orcid.org/0000-0001-9389-870X</orcidid></search><sort><creationdate>20230509</creationdate><title>Visible light-mediated metal-free alkyl Suzuki-Miyaura coupling of alkyl halides and alkenylboronic acids/esters: a green method for the synthesis of allyl difluoride derivatives</title><author>Qu, Chuan-Hua ; Yan, Xiao ; Li, Shu-Ting ; Liu, Jian-Bo ; Xu, Zhi-Gang ; Chen, Zhong-Zhu ; Tang, Dian-Yong ; Liu, Huan-Xiang ; Song, Gui-Ting</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-72eae4918bc7e703ebb005ad3fd1dd8d6c3bc6c7a0e09833f8847f01dd06cb723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Amines</topic><topic>Chemical reactions</topic><topic>Coupling</topic><topic>Covalent bonds</topic><topic>Difluorides</topic><topic>Esters</topic><topic>Green chemistry</topic><topic>Halides</topic><topic>Ketones</topic><topic>Streamlining</topic><topic>Substrates</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qu, Chuan-Hua</creatorcontrib><creatorcontrib>Yan, Xiao</creatorcontrib><creatorcontrib>Li, Shu-Ting</creatorcontrib><creatorcontrib>Liu, Jian-Bo</creatorcontrib><creatorcontrib>Xu, Zhi-Gang</creatorcontrib><creatorcontrib>Chen, Zhong-Zhu</creatorcontrib><creatorcontrib>Tang, Dian-Yong</creatorcontrib><creatorcontrib>Liu, Huan-Xiang</creatorcontrib><creatorcontrib>Song, Gui-Ting</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>Qu, Chuan-Hua</au><au>Yan, Xiao</au><au>Li, Shu-Ting</au><au>Liu, Jian-Bo</au><au>Xu, Zhi-Gang</au><au>Chen, Zhong-Zhu</au><au>Tang, Dian-Yong</au><au>Liu, Huan-Xiang</au><au>Song, Gui-Ting</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible light-mediated metal-free alkyl Suzuki-Miyaura coupling of alkyl halides and alkenylboronic acids/esters: a green method for the synthesis of allyl difluoride derivatives</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2023-05-09</date><risdate>2023</risdate><volume>25</volume><issue>9</issue><spage>3453</spage><epage>3461</epage><pages>3453-3461</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>The Suzuki-Miyaura reaction has greatly facilitated the construction of C-C bonds and is well appreciated in medicinal chemistry, yet transition metal residues in this process are an unavoidable challenge. Herein, we report the first visible-light-driven photocatalyst-free coupling reaction of alkenylboronic acids/esters with α-bromodifluoroacylarenes, providing streamlining access to a series of Suzuki coupling products. The reactions proceed under metal-free conditions with a wide substrate scope. Mechanistic experiments and DFT calculation studies revealed that halogen bonding interactions, mainly generated
in situ
between α-bromodifluoroacylarenes and tertiary amines, could promote the C
sp
3
-Br bond homolytic cleavage from difluorobromoaryl ketones.
Halogen bonding-assisted C
sp
3
-Br homolysis and bromine radical-mediated oxidative deboronation make visible-light-driven photocatalyst-free alkyl Suzuki-Miyaura coupling of alkenylboronic acids/esters with α-bromodifluoroacylarenes accessible.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d3gc00368j</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-3821-3963</orcidid><orcidid>https://orcid.org/0000-0001-9389-870X</orcidid></addata></record> |
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| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2023-05, Vol.25 (9), p.3453-3461 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amines Chemical reactions Coupling Covalent bonds Difluorides Esters Green chemistry Halides Ketones Streamlining Substrates Transition metals |
| title | Visible light-mediated metal-free alkyl Suzuki-Miyaura coupling of alkyl halides and alkenylboronic acids/esters: a green method for the synthesis of allyl difluoride derivatives |
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