Sustainable electrochemical dehydrogenative C(sp)-H mono/di-alkylations
Catalyst-free, direct electrooxidative phenol derivatives C(sp 3 )-H mono- and di-alkylation reaction have been developed. In contrast to previous typical oxidative and electrochemical coupling, this electrosynthetic approach enables selective mono- and di-alkylations through metal- and external oxi...
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Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2022-03, Vol.24 (6), p.2483-2491 |
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container_title | Green chemistry : an international journal and green chemistry resource : GC |
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creator | He, Jin-Yu Qian, Wei-Feng Wang, Yan-Zhao Yao, Chaochao Wang, Nana Liu, Huilin Zhong, Bing Zhu, Cuiju Xu, Hao |
description | Catalyst-free, direct electrooxidative phenol derivatives C(sp
3
)-H mono- and di-alkylation reaction have been developed. In contrast to previous typical oxidative and electrochemical coupling, this electrosynthetic approach enables selective mono- and di-alkylations through metal- and external oxidant-free mild conditions
via
easily available electrodes. Advances of this strategy were proven by an unparalleled broad substrate scope for efficient C-C, C-N, C-O bond formation as well as excellent site- and regioselectivity. The electrochemical selective alkylations were devoid of additional electrolytes, could be conducted on a gram scale, and provided the enone products by cascade electrooxidative dehydrogenation, which highlight a notable potential for further late-stage diversification. Detailed mechanistic studies allowed to delineate the exact profile of the generation of the mono- and di-alkylation events.
Catalyst-free, direct electrooxidative phenol derivatives C(sp
3
)-H mono- and di-alkylation reaction have been developed. |
doi_str_mv | 10.1039/d1gc04479f |
format | Article |
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3
)-H mono- and di-alkylation reaction have been developed. In contrast to previous typical oxidative and electrochemical coupling, this electrosynthetic approach enables selective mono- and di-alkylations through metal- and external oxidant-free mild conditions
via
easily available electrodes. Advances of this strategy were proven by an unparalleled broad substrate scope for efficient C-C, C-N, C-O bond formation as well as excellent site- and regioselectivity. The electrochemical selective alkylations were devoid of additional electrolytes, could be conducted on a gram scale, and provided the enone products by cascade electrooxidative dehydrogenation, which highlight a notable potential for further late-stage diversification. Detailed mechanistic studies allowed to delineate the exact profile of the generation of the mono- and di-alkylation events.
Catalyst-free, direct electrooxidative phenol derivatives C(sp
3
)-H mono- and di-alkylation reaction have been developed.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/d1gc04479f</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alkylation ; Catalysts ; Dehydrogenation ; Electrochemistry ; Electrolytes ; Green chemistry ; Oxidants ; Oxidizing agents ; Phenols ; Regioselectivity ; Substrates</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2022-03, Vol.24 (6), p.2483-2491</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-963b0f4a1fc447efe4c723d11b65cc927194493dc85d7dfda456a517b7aacd103</citedby><cites>FETCH-LOGICAL-c281t-963b0f4a1fc447efe4c723d11b65cc927194493dc85d7dfda456a517b7aacd103</cites><orcidid>0000-0001-9685-7364</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>He, Jin-Yu</creatorcontrib><creatorcontrib>Qian, Wei-Feng</creatorcontrib><creatorcontrib>Wang, Yan-Zhao</creatorcontrib><creatorcontrib>Yao, Chaochao</creatorcontrib><creatorcontrib>Wang, Nana</creatorcontrib><creatorcontrib>Liu, Huilin</creatorcontrib><creatorcontrib>Zhong, Bing</creatorcontrib><creatorcontrib>Zhu, Cuiju</creatorcontrib><creatorcontrib>Xu, Hao</creatorcontrib><title>Sustainable electrochemical dehydrogenative C(sp)-H mono/di-alkylations</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>Catalyst-free, direct electrooxidative phenol derivatives C(sp
3
)-H mono- and di-alkylation reaction have been developed. In contrast to previous typical oxidative and electrochemical coupling, this electrosynthetic approach enables selective mono- and di-alkylations through metal- and external oxidant-free mild conditions
via
easily available electrodes. Advances of this strategy were proven by an unparalleled broad substrate scope for efficient C-C, C-N, C-O bond formation as well as excellent site- and regioselectivity. The electrochemical selective alkylations were devoid of additional electrolytes, could be conducted on a gram scale, and provided the enone products by cascade electrooxidative dehydrogenation, which highlight a notable potential for further late-stage diversification. Detailed mechanistic studies allowed to delineate the exact profile of the generation of the mono- and di-alkylation events.
Catalyst-free, direct electrooxidative phenol derivatives C(sp
3
)-H mono- and di-alkylation reaction have been developed.</description><subject>Alkylation</subject><subject>Catalysts</subject><subject>Dehydrogenation</subject><subject>Electrochemistry</subject><subject>Electrolytes</subject><subject>Green chemistry</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><subject>Phenols</subject><subject>Regioselectivity</subject><subject>Substrates</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpFkNFLwzAQh4MoOKcvvgsFX1Soy7VpsjxKdZsw8EF9Lukl2Tq7ZiadsP_e6GQ-3cF93P3uI-QS6D3QXI40LJAyJqQ9IgNgPE9lJujxoefZKTkLYUUpgOBsQKav29CrplN1axLTGuy9w6VZN6jaRJvlTnu3MJ3qmy-TlDdhc5vOkrXr3Eg3qWo_dm0cuS6ckxOr2mAu_uqQvE-e3spZOn-ZPpcP8xSzMfSp5HlNLVNgMaY01jAUWa4Bal4gxqwgGZO5xnGhhbZasYKrAkQtlEIdXxyS6_3ejXefWxP6auW2vosnq4wzKgWnkkXqbk-hdyF4Y6uNb9bK7yqg1Y-o6hGm5a-oSYSv9rAPeOD-Rebf-dFk-Q</recordid><startdate>20220321</startdate><enddate>20220321</enddate><creator>He, Jin-Yu</creator><creator>Qian, Wei-Feng</creator><creator>Wang, Yan-Zhao</creator><creator>Yao, Chaochao</creator><creator>Wang, Nana</creator><creator>Liu, Huilin</creator><creator>Zhong, Bing</creator><creator>Zhu, Cuiju</creator><creator>Xu, Hao</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/0000-0001-9685-7364</orcidid></search><sort><creationdate>20220321</creationdate><title>Sustainable electrochemical dehydrogenative C(sp)-H mono/di-alkylations</title><author>He, Jin-Yu ; Qian, Wei-Feng ; Wang, Yan-Zhao ; Yao, Chaochao ; Wang, Nana ; Liu, Huilin ; Zhong, Bing ; Zhu, Cuiju ; Xu, Hao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-963b0f4a1fc447efe4c723d11b65cc927194493dc85d7dfda456a517b7aacd103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkylation</topic><topic>Catalysts</topic><topic>Dehydrogenation</topic><topic>Electrochemistry</topic><topic>Electrolytes</topic><topic>Green chemistry</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><topic>Phenols</topic><topic>Regioselectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Jin-Yu</creatorcontrib><creatorcontrib>Qian, Wei-Feng</creatorcontrib><creatorcontrib>Wang, Yan-Zhao</creatorcontrib><creatorcontrib>Yao, Chaochao</creatorcontrib><creatorcontrib>Wang, Nana</creatorcontrib><creatorcontrib>Liu, Huilin</creatorcontrib><creatorcontrib>Zhong, Bing</creatorcontrib><creatorcontrib>Zhu, Cuiju</creatorcontrib><creatorcontrib>Xu, Hao</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>He, Jin-Yu</au><au>Qian, Wei-Feng</au><au>Wang, Yan-Zhao</au><au>Yao, Chaochao</au><au>Wang, Nana</au><au>Liu, Huilin</au><au>Zhong, Bing</au><au>Zhu, Cuiju</au><au>Xu, Hao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sustainable electrochemical dehydrogenative C(sp)-H mono/di-alkylations</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2022-03-21</date><risdate>2022</risdate><volume>24</volume><issue>6</issue><spage>2483</spage><epage>2491</epage><pages>2483-2491</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>Catalyst-free, direct electrooxidative phenol derivatives C(sp
3
)-H mono- and di-alkylation reaction have been developed. In contrast to previous typical oxidative and electrochemical coupling, this electrosynthetic approach enables selective mono- and di-alkylations through metal- and external oxidant-free mild conditions
via
easily available electrodes. Advances of this strategy were proven by an unparalleled broad substrate scope for efficient C-C, C-N, C-O bond formation as well as excellent site- and regioselectivity. The electrochemical selective alkylations were devoid of additional electrolytes, could be conducted on a gram scale, and provided the enone products by cascade electrooxidative dehydrogenation, which highlight a notable potential for further late-stage diversification. Detailed mechanistic studies allowed to delineate the exact profile of the generation of the mono- and di-alkylation events.
Catalyst-free, direct electrooxidative phenol derivatives C(sp
3
)-H mono- and di-alkylation reaction have been developed.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1gc04479f</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-9685-7364</orcidid></addata></record> |
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source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
subjects | Alkylation Catalysts Dehydrogenation Electrochemistry Electrolytes Green chemistry Oxidants Oxidizing agents Phenols Regioselectivity Substrates |
title | Sustainable electrochemical dehydrogenative C(sp)-H mono/di-alkylations |
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