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Ligand-Free Ru-Catalyzed Direct sp 3 C-H Alkylation of Fluorene Using Alcohols
The sp C-H alkylation of 9 -fluorene using alcohol and a Ru catalyst via the borrowing hydrogen concept has been described. This reaction was catalyzed by the [Ru( -cymene)Cl ] complex (3 mol %) and exhibited a broad reaction scope with different alcohols, allowing primary and secondary alcohols to...
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Published in: | Journal of organic chemistry 2020-02, Vol.85 (4), p.2277-2290 |
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container_title | Journal of organic chemistry |
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creator | Shaikh, Moseen A Agalave, Sandip G Ubale, Akash S Gnanaprakasam, Boopathy |
description | The sp
C-H alkylation of 9
-fluorene using alcohol and a Ru catalyst via the borrowing hydrogen concept has been described. This reaction was catalyzed by the [Ru(
-cymene)Cl
]
complex (3 mol %) and exhibited a broad reaction scope with different alcohols, allowing primary and secondary alcohols to be employed as nonhazardous and greener alkylating agents with the formation of environmentally benign water as a byproduct. A variety of 9
-fluorene underwent selective and exclusive mono-C9-alkylation with primary alcohols in good to excellent isolated yield (26 examples, 50-92% yield), whereas this reaction with secondary alcohols in the absence of any external oxidants furnished the tetrasubstituted alkene as the major product. Furthermore, a base-mediated C-H hydroxylation of the synthesized 9
-fluorene derivatives afforded 9
-hydroxy-functionalized quaternary fluorene derivatives in excellent yield. |
doi_str_mv | 10.1021/acs.joc.9b02913 |
format | article |
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C-H alkylation of 9
-fluorene using alcohol and a Ru catalyst via the borrowing hydrogen concept has been described. This reaction was catalyzed by the [Ru(
-cymene)Cl
]
complex (3 mol %) and exhibited a broad reaction scope with different alcohols, allowing primary and secondary alcohols to be employed as nonhazardous and greener alkylating agents with the formation of environmentally benign water as a byproduct. A variety of 9
-fluorene underwent selective and exclusive mono-C9-alkylation with primary alcohols in good to excellent isolated yield (26 examples, 50-92% yield), whereas this reaction with secondary alcohols in the absence of any external oxidants furnished the tetrasubstituted alkene as the major product. Furthermore, a base-mediated C-H hydroxylation of the synthesized 9
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-hydroxy-functionalized quaternary fluorene derivatives in excellent yield.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.9b02913</identifier><identifier>PMID: 31905282</identifier><language>eng</language><publisher>United States</publisher><ispartof>Journal of organic chemistry, 2020-02, Vol.85 (4), p.2277-2290</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1092-c93cdaa7c1442d58f78c41c3702744461c71aef8310eaf595d68a6b3a66c28423</citedby><cites>FETCH-LOGICAL-c1092-c93cdaa7c1442d58f78c41c3702744461c71aef8310eaf595d68a6b3a66c28423</cites><orcidid>0000-0002-3047-9636</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31905282$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shaikh, Moseen A</creatorcontrib><creatorcontrib>Agalave, Sandip G</creatorcontrib><creatorcontrib>Ubale, Akash S</creatorcontrib><creatorcontrib>Gnanaprakasam, Boopathy</creatorcontrib><title>Ligand-Free Ru-Catalyzed Direct sp 3 C-H Alkylation of Fluorene Using Alcohols</title><title>Journal of organic chemistry</title><addtitle>J Org Chem</addtitle><description>The sp
C-H alkylation of 9
-fluorene using alcohol and a Ru catalyst via the borrowing hydrogen concept has been described. This reaction was catalyzed by the [Ru(
-cymene)Cl
]
complex (3 mol %) and exhibited a broad reaction scope with different alcohols, allowing primary and secondary alcohols to be employed as nonhazardous and greener alkylating agents with the formation of environmentally benign water as a byproduct. A variety of 9
-fluorene underwent selective and exclusive mono-C9-alkylation with primary alcohols in good to excellent isolated yield (26 examples, 50-92% yield), whereas this reaction with secondary alcohols in the absence of any external oxidants furnished the tetrasubstituted alkene as the major product. Furthermore, a base-mediated C-H hydroxylation of the synthesized 9
-fluorene derivatives afforded 9
-hydroxy-functionalized quaternary fluorene derivatives in excellent yield.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNo90E1PAjEQBuDGaATRszfTP1CY6dduj2QVMSGaGDlvSreLi8uWtHDAX-8a0LnMYd53Dg8h9whjBI4T69J4E9zYrIAbFBdkiIoD0wbkJRkCcM4E12JAblLaQD9KqWsyEGhA8ZwPyeuiWduuYrPoPX0_sMLubXv89hV9bKJ3e5p2VNCCzem0_Tq2dt-EjoaaztpDiL7zdJmabt0fXfgMbbolV7Vtk7877xFZzp4-ijlbvD2_FNMFcwiGM2eEq6zNHErJK5XXWe4kOpEBz6SUGl2G1te5QPC2VkZVOrd6JazWjueSixGZnP66GFKKvi53sdnaeCwRyl-Zspcpe5nyLNM3Hk6N3WG19dV__o9C_ADmzF6B</recordid><startdate>20200221</startdate><enddate>20200221</enddate><creator>Shaikh, Moseen A</creator><creator>Agalave, Sandip G</creator><creator>Ubale, Akash S</creator><creator>Gnanaprakasam, Boopathy</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-3047-9636</orcidid></search><sort><creationdate>20200221</creationdate><title>Ligand-Free Ru-Catalyzed Direct sp 3 C-H Alkylation of Fluorene Using Alcohols</title><author>Shaikh, Moseen A ; Agalave, Sandip G ; Ubale, Akash S ; Gnanaprakasam, Boopathy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1092-c93cdaa7c1442d58f78c41c3702744461c71aef8310eaf595d68a6b3a66c28423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shaikh, Moseen A</creatorcontrib><creatorcontrib>Agalave, Sandip G</creatorcontrib><creatorcontrib>Ubale, Akash S</creatorcontrib><creatorcontrib>Gnanaprakasam, Boopathy</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shaikh, Moseen A</au><au>Agalave, Sandip G</au><au>Ubale, Akash S</au><au>Gnanaprakasam, Boopathy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ligand-Free Ru-Catalyzed Direct sp 3 C-H Alkylation of Fluorene Using Alcohols</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J Org Chem</addtitle><date>2020-02-21</date><risdate>2020</risdate><volume>85</volume><issue>4</issue><spage>2277</spage><epage>2290</epage><pages>2277-2290</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The sp
C-H alkylation of 9
-fluorene using alcohol and a Ru catalyst via the borrowing hydrogen concept has been described. This reaction was catalyzed by the [Ru(
-cymene)Cl
]
complex (3 mol %) and exhibited a broad reaction scope with different alcohols, allowing primary and secondary alcohols to be employed as nonhazardous and greener alkylating agents with the formation of environmentally benign water as a byproduct. A variety of 9
-fluorene underwent selective and exclusive mono-C9-alkylation with primary alcohols in good to excellent isolated yield (26 examples, 50-92% yield), whereas this reaction with secondary alcohols in the absence of any external oxidants furnished the tetrasubstituted alkene as the major product. Furthermore, a base-mediated C-H hydroxylation of the synthesized 9
-fluorene derivatives afforded 9
-hydroxy-functionalized quaternary fluorene derivatives in excellent yield.</abstract><cop>United States</cop><pmid>31905282</pmid><doi>10.1021/acs.joc.9b02913</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-3047-9636</orcidid></addata></record> |
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title | Ligand-Free Ru-Catalyzed Direct sp 3 C-H Alkylation of Fluorene Using Alcohols |
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